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Pure Appl. Chem., 1989, Vol. 61, No. 7, pp. 1257-1270

http://dx.doi.org/10.1351/pac198961071257

Recent developments in the synthesis of glycoconjugates

R. R. Schmidt

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  • Zhu Danyang, Baryal Kedar N., Adhikari Surya, Zhu Jianglong: Direct Synthesis of 2-Deoxy-β-Glycosides via Anomeric O-Alkylation with Secondary Electrophiles. J. Am. Chem. Soc. 2014, 136, 3172. <http://dx.doi.org/10.1021/ja4116956>
  • Koch Stefan, Schollmeyer Dieter, Löwe Holger, Kunz Horst: C -Glycosyl Amino Acids through Hydroboration-Cross-Coupling of exo -Glycals and Their Application in Automated Solid-Phase Synthesis. Chem. Eur. J. 2013, 19, 7020. <http://dx.doi.org/10.1002/chem.201300150>
  • Pfaffe Matthias, Mahrwald Rainer: Direct Glycosylation of Unprotected and Unactivated Carbohydrates under Mild Conditions. Org Lett 2012, 14, 792. <http://dx.doi.org/10.1021/ol203329u>
  • Pertel Sergey S., Gorkunenko Oksana A., Kakayan Elena S., Chirva Vasily Ja.: Synthesis of 1,2-cis- and 1,2-trans-glycosides of 2-acetamido-4,6-O-benzylidene-2-deoxy-d-glucopyranose by anomeric O-alkylation. Carbohydrate Research 2011, 346, 685. <http://dx.doi.org/10.1016/j.carres.2011.01.016>
  • Bera Smritilekha, Linhardt Robert J.: Design and Synthesis of Unnatural Heparosan and Chondroitin Building Blocks. J Org Chem 2011, 76, 3181. <http://dx.doi.org/10.1021/jo200076z>
  • O-Glycosid-Synthesen. Nachr Chem Tech Lab 2010, 39, 675. <http://dx.doi.org/10.1002/nadc.19910390610>
  • Frąckowiak Anna, Skibiński Przemysław, Gaweł Wiesław, Zaczyńska Ewa, Czarny Anna, Gancarz Roman: Synthesis of glycoside derivatives of hydroxyanthraquinone with ability to dissolve and inhibit formation of crystals of calcium oxalate. Potential compounds in kidney stone therapy. Eur J Med Chem 2010, 45, 1001. <http://dx.doi.org/10.1016/j.ejmech.2009.11.042>
  • Gräber Martin, Andersson Mats, Rundbäck Fabian, Pozzo Tania, Karlsson Eva Nordberg, Adlercreutz Patrick: A novel direct screening method for alkyl glucoside production by glucosidases expressed in E. coli in 96-well plates. Journal of Biotechnology 2010, 145, 186. <http://dx.doi.org/10.1016/j.jbiotec.2009.11.005>
  • Khaja Sirajud D., Kumar Vipin, Ahmad Misbah, Xue Jun, Matta Khushi L.: Novel galactosyl donor with 2-naphthylmethyl (NAP) as the non-participating group at C-2 position: efficient synthesis of α-galactosyl ceramide. Tetrahetron Lett 2010, 51, 4411. <http://dx.doi.org/10.1016/j.tetlet.2010.06.071>
  • Reddy Maddi Sridhar, Zhang Hongxing, Phoenix Serge, Deslongchamps Pierre: Total Synthesis of Ouabagenin and Ouabain. Chem Asian J 2009, 4, 725. <http://dx.doi.org/10.1002/asia.200800429>
  • Komano Kazuo, Shimamura Satoshi, Norizuki Yutaro, Zhao Donglin, Kabuto Chizuko, Sato Itaru, Hirama Masahiro: Total Synthesis and Structure Revision of the (−)-Maduropeptin Chromophore. J Am Chem Soc 2009, 131, 12072. <http://dx.doi.org/10.1021/ja905397p>
  • GERZ M., MATTER H., KESSLER H.: Synthesis and solution structure of an S-glycosylated cyclic hexapeptide : Evidence for conformational change induced by glycosylation. Int J Pept Prot Res 2009, 43, 248. <http://dx.doi.org/10.1111/j.1399-3011.1994.tb00387.x>
  • Zhang Hongxing, Sridhar Reddy Maddi, Phoenix Serge, Deslongchamps Pierre: Total Synthesis of Ouabagenin and Ouabain. Angew Chem 2008, 120, 1292. <http://dx.doi.org/10.1002/ange.200704959>
  • Zhang Hongxing, Sridhar Reddy Maddi, Phoenix Serge, Deslongchamps Pierre: Total Synthesis of Ouabagenin and Ouabain. Angew Chem Int Ed 2008, 47, 1272. <http://dx.doi.org/10.1002/anie.200704959>
  • Lian Gaoyan, Gao Qi, Lin Feng: Synthesis of fructofuranosides: efficient glycosylation with N-phenyltrifluoroacetimidate as the leaving group. Carbohydrates Research 2008, 343, 2992. <http://dx.doi.org/10.1016/j.carres.2008.09.001>
  • Hou Chuan-Jin, Liang Xiao-Mei, Wu Jing-Ping, Huang Jia-Xing, Zhang Jian-Jun, Wang Dao-Quan: Resolution of racemic 12-hydroxyl-1,15-pentadecanlactam using d-glucose derivative as a chiral auxiliary. Tet Asymm 2008, 19, 379. <http://dx.doi.org/10.1016/j.tetasy.2008.01.007>
  • Costantino Valeria, de Rosa Caterina, Fattorusso Ernesto, Imperatore Concetta, Mangoni Alfonso, Irace Carlo, Maffettone Carmen, Capasso Domenica, Malorni Livia, Palumbo Rosanna: Oreacerebrosides: Bioactive Cerebrosides with a Triunsaturated Sphingoid Base from the Sea StarOreaster reticulatus. Eur J Org Chem 2007, 2007, 5277. <http://dx.doi.org/10.1002/ejoc.200700390>
  • Sancéau Jean-Yves, Larouche Denis, Caron Brigitte, Bélanger Patrick, Coquet Agnès, Bélanger Alain, Labrie Fernand, Gauthier Sylvain: Synthesis and deuterium labelling of the pure selective estrogen receptor modulator (SERM) acolbifene glucuronides. J Labelled Cpd Radiopharm 2007, 50, 197. <http://dx.doi.org/10.1002/jlcr.1260>
  • Falconer Robert A., Toth Istvan: Design, synthesis and biological evaluation of novel lipoamino acid-based glycolipids for oral drug delivery. biorg med chem 2007, 15, 7012. <http://dx.doi.org/10.1016/j.bmc.2007.07.048>
  • Álvarez-Micó Xavier, Calvete Mario J.F., Hanack Michael, Ziegler Thomas: A new glycosidation method through nitrite displacement on substituted nitrobenzenes. Carbohydrates Research 2007, 342, 440. <http://dx.doi.org/10.1016/j.carres.2006.11.017>
  • O-Glycosylation in the Solid to Solid State. Bulletin of the Korean Chemical Society 2007, 28, 2493. <http://dx.doi.org/10.5012/bkcs.2007.28.12.2493>
  • Tietze Lutz F., Gericke Kersten M., Güntner Carlos: First Total Synthesis of the Bioactive Anthraquinone Kwanzoquinone C and Related Natural Products by a Diels–Alder Approach. Eur J Org Chem 2006, 2006, 4910. <http://dx.doi.org/10.1002/ejoc.200600634>
  • Greilich Ulrike, Brescello Roberto, Jung Karl-Heinz, Schmidt Richard R.: Glycosyl Imidates, 74. Synthesis of Ganglioside GM1 via a GM3 Intermediate. Liebigs Ann /Recueil 2006, 1996, 663. <http://dx.doi.org/10.1002/jlac.199619960504>
  • Schmidt Richard R., Jankowski Karin: New Types of Nonionic Surfactants with Sugar Head Groups. Liebigs Ann /Recueil 2006, 1996, 867. <http://dx.doi.org/10.1002/jlac.199619960603>
  • Terjung Andreas, Jung Karl-Heinz, Schmidt Richard R.: Anomeric O-Alkylation, 15. New 2/1-Type Surfactants by Anomeric O-Alkylation of Mannofuranose. Liebigs Ann /Recueil 2006, 1996, 1313. <http://dx.doi.org/10.1002/jlac.199619960811>
  • Fekete Anikó, Gyergyói Katalin, Kövér Katalin E., Bajza István, Lipták András: Preparation of the pentasaccharide hapten of the GPL of Mycobacterium avium serovar 19 by achieving the glycosylation of a tertiary hydroxyl group. Carbohydrates Research 2006, 341, 1312. <http://dx.doi.org/10.1016/j.carres.2006.04.038>
  • Yang Xiaoliang, Sun Yang, Xu Qiang, Guo Zijian: Synthesis and immunosuppressive activity of l-rhamnopyranosyl flavonoids. Org Biomol Chem 2006, 4, 2483. <http://dx.doi.org/10.1039/b604521a>
  • Pellissier Hélène: Use of O-glycosylation in total synthesis. Tetrahedron 2005, 61, 2947. <http://dx.doi.org/10.1016/j.tet.2005.01.070>
  • Kim Seongkon, Wu Jane Y., Zhang Zhoupeng, Tang Wei, Doss George A., Dean Brian J., DiNinno Frank, Hammond Milton L.: Estrogen Receptor Ligands. 12. Synthesis of the Major Metabolites of an ERα-Selective, Dihydrobenzoxathiin Antagonist for Osteoporosis. Org Lett 2005, 7, 411. <http://dx.doi.org/10.1021/ol047741f>
  • Simo Ondrej, Michael Katja, Yoshida Wesley, Chertkov Vyacheslav A., Gross Paul H.: Selective Reductions of C‐(4,6‐O‐Benzylidene‐β‐d‐glucopyranosyl) Nitromethane. Synth Common 2005, 35, 1589. <http://dx.doi.org/10.1081/SCC-200061554>
  • Chen Langqiu, Kong Fanzuo: Unusual α-glycosylation with galactosyl donors with a C2 ester capable of neighboring group participation. Tetrahetron Lett 2003, 44, 3691. <http://dx.doi.org/10.1016/S0040-4039(03)00673-7>
  • Díaz de Vivar María E., Seldes Alicia M., Maier Marta S.: Two novel glucosylceramides from gonads and body walls of the patagonian starfish Allostichaster inaequalis. Lipid 2002, 37, 597. <http://dx.doi.org/10.1007/s11745-002-0938-7>
  • Zeng Ying, Ning Jun, Kong Fanzuo: Pure α-linked products can be obtained in high yields in glycosylation with glucosyl trichloroacetimidate donors with a C2 ester capable of neighboring group participation. Tetrahetron Lett 2002, 43, 3729. <http://dx.doi.org/10.1016/S0040-4039(02)00584-1>
  • Mondal Ejabul, Barua Pankaj M. Bujar, Bose Gopal, Khan Abu T.: A Useful and Convenient Synthetic Procedure for Hydrolysis of Thioglycosides. Chem Lett 2002, 210. <http://dx.doi.org/10.1246/cl.2002.210>
  • Pouységu Laurent, De Jéso Bernard, Lartigue Jean-Claude, Pétraud Michel, Ratier Max: Structural Analysis of Partially Acetylated Glycosides by Refocused-Decoupled Insensitive Nuclei Enhanced by Polarization Transfer (INEPT) Experiments: A Qualitative and Quantitative Method. Chem Pharm Bull 2002, 50, 1114. <http://dx.doi.org/10.1248/cpb.50.1114>
  • Li Xiaoliu, Ohtake Hiro, Takahashi Hideyo, Ikegami Shiro: A facile synthesis of 1′-C-alkyl-α-disaccharides from 1-C-alkyl-hexopyranoses and methyl 1-C-methyl-hexopyranosides. Tetrahedron 2001, 57, 4297. <http://dx.doi.org/10.1016/S0040-4020(01)00321-0>
  • Vauzeilles Boris, Dausse Bruno, Palmier Sara, Beau Jean-Marie: A one-step β-selective glycosylation of N-acetyl glucosamine and recombinant chitooligosaccharides. Tetrahetron Lett 2001, 42, 7567. <http://dx.doi.org/10.1016/S0040-4039(01)01594-5>
  • Dufner Gesche, Schwörer Ralf, Müller Bernd, Schmidt Richard R.: Base- and Sugar-Modified Cytidine MonophosphateN-Acetylneuraminic Acid (CMP-Neu5Ac) Analogues - Synthesis and Studies with α(2-6)-Sialyltransferase from Rat Liver. Eur J Org Chem 2000, 2000, 1467. <http://dx.doi.org/10.1002/(SICI)1099-0690(200004)2000:8<1467::AID-EJOC1467>3.0.CO;2-E>
  • Medgyes Adél, Bajza István, Farkas Erzsébet, Pozsgay Vince, Lipták András: Synthetic Studies Towards the O-Specific Polysaccharide of Shigella Sonnei. J Carbohydr Chem 2000, 19, 285. <http://dx.doi.org/10.1080/07328300008544079>
  • Bousquet Ennio, Spadaro Angelo, Pappalardo Maria S., Bernardini Renato, Romeo Rosalba, Panza Luigi, Ronsisvalle Giuseppe: Synthesis and Immunostimulating Activity of A Thioglycolipopeptide Glycomimetic As A Potential Anticancer Vaccine Derived From Tn Antigen. J Carbohydr Chem 2000, 19, 527. <http://dx.doi.org/10.1080/07328300008544097>
  • Zawisza Anna, Kryczka Boguslaw, Lhoste Paul, Porwanski Stanislaw, Sinou Denis: Efficient Palladium(0)-Catalyzed Synthesis of Alkenyl 1-Thioglycosides and Thiodisaccharides. J Carbohydr Chem 2000, 19, 795. <http://dx.doi.org/10.1080/07328300008544118>
  • Azumaya Isao, Niwa Toshihiro, Kotani Masaomi, Iimori Takamasa, Ikegami Shiro: An efficient synthesis of mixed β-carbonates of acyl-protected sugar and their decarboxylative glycosidation promoted by trimethylsilyl trifluoromethanesulfonate. Tetrahedron Letters 1999, 40, 4683. <http://dx.doi.org/10.1016/S0040-4039(99)00843-6>
  • Gardossi Lucia, Khan Riaz, Konowicz Paul A., Gropen Line, Paulsen Berit S.: Enzymatic regioselective deprotection of peracetylated mono- and disaccharides. Mol Catal B Enzym 1999, 6, 89. <http://dx.doi.org/10.1016/S1381-1177(98)00130-1>
  • Huchel Ursula, Schmidt Christoph, Schmidt Richard R.: Synthesis of Hetaryl Glycosides and Their Glycosyl Donor Properties. Eur J Org Chem 1998, 1998, 1353. <http://dx.doi.org/10.1002/(SICI)1099-0690(199807)1998:7<1353::AID-EJOC1353>3.0.CO;2-C>
  • Tietze Lutz F., Gretzke Dirk: Synthesis of Specifically Labelled Ganglioside [1c-13C]-GM3. Eur J Org Chem 1998, 1998, 1895. <http://dx.doi.org/10.1002/(SICI)1099-0690(199809)1998:9<1895::AID-EJOC1895>3.0.CO;2-S>
  • Durán Rosario, Zubía Eva, Ortega María J., Naranjo Santiago, Salvá Javier: Phallusides, new glucosphingolipids from the ascidian Phallusia fumigata. Tetrahedron 1998, 54, 14597. <http://dx.doi.org/10.1016/S0040-4020(98)00917-X>
  • Martin Jaime, Jaramillo G Luz Marina, Wang Peng George: Efficient synthesis of α-Aldopyranosyl cyanides via radical cyanation reactions. Tetrahetron Lett 1998, 39, 5927. <http://dx.doi.org/10.1016/S0040-4039(98)01213-1>
  • Regeling Henk, Sunghwa Fortunatus, Zwanenburg Binne, de Gelder René, Chittenden Gordon J.F: Synthesis and reactions of some derivatives of (3,6S,9R,10R,11S)-1,4,7-trioxaspiro[5,5]undecane-3,9,10,11-tetrol: novel quasi-saccharides1Presented at the 2nd International Meeting of the Portuguese Carbohydrate Chemistry Group, Porto, Portugal, 21–25 September 1997.1. Carbohyd Polymers 1998, 37, 323. <http://dx.doi.org/10.1016/S0144-8617(98)00078-2>
  • Vaccaro Wayne D., Davis Harry R.: Sugar-substituted 2-azetidinone cholesterol absorption inhibitors: Enhanced potency by modification of the sugar. Biorg Med Chem Lett 1998, 8, 313. <http://dx.doi.org/10.1016/S0960-894X(98)00008-0>
  • Robina Inmaculada, Gómez-Bujedo Silvia, Fernández-Bolaños José G., Fuentes José: Introduction of C-Sulfonate Groups into Disaccharide Derivatives. Synth Common 1998, 28, 2379. <http://dx.doi.org/10.1080/00397919808004290>
  • Frappa Isabelle, Kryczka Boguslaw, Lhoste Paul, Porwanski Stanislaw, Sinou Denis, Zawisza Anna: Palladium(0)-Mediated Synthesis of Acetylated Unsaturated 1,4-Disaccharides. J Carbohydr Chem 1998, 17, 1117. <http://dx.doi.org/10.1080/07328309808001888>
  • Matsuo Ichiro, Miyazaki Tatsuo, Isomura Megumi, Sakakibara Tohru, Ajisaka Katsumi: A Short, Efficient Synthesis of the Octamannan Residue of High Mannose Type Sugar Chains. J Carbohydr Chem 1998, 17, 1249. <http://dx.doi.org/10.1080/07328309808001897>
  • Finizia Gabriella: On the Synthesis of Aminoglycosides of Cardioactive Steroids: A Study Directed Towards β- Selective Glycosylations of 3-Aminodigitoxose with Digitoxigenin Analogues. J Carbohydr Chem 1998, 17, 75. <http://dx.doi.org/10.1080/07328309808005770>
  • Käsbeck Ludwig, Kessler Horst: Synthesis ofS-α-D-GlucosylatedL-Cysteine – A NovelS-Glycosyl Amino Acid. Liebigs Ann /Recueil 1997, 1997, 165. <http://dx.doi.org/10.1002/jlac.199719970123>
  • Käsbeck Ludwig, Kessler Horst: Convenient Syntheses of 2,3,4,6-Tetra-O-AlkylatedD-Glucose andD-Galactose. Liebigs Ann /Recueil 1997, 1997, 169. <http://dx.doi.org/10.1002/jlac.199719970124>
  • Zhang Hong, Wang Yali, Thürmer René, Meisenbach Mark, Voelter Wolfgang: Stereoselective Synthesis of the Core Structure of the Nephritogenoside Glycopeptide. Liebigs Ann /Recueil 1997, 1997, 1871. <http://dx.doi.org/10.1002/jlac.199719970910>
  • Matsuo Ichiro, Isomura Megumi, Miyazaki Tatsuo, Sakakibara Tohru, Ajisaka Katsumi: Chemoenzymatic synthesis of the branched oligosaccharides which correspond to the core structures of N-linked sugar chains. Carbohydrates Research 1997, 305, 401. <http://dx.doi.org/10.1016/S0008-6215(97)10001-5>
  • Magaud Didier, Grandjean Cyrille, Doutheau Alain, Anker Daniel, Shevchik Vladimir, Cotte-Pattat Nicole, Robert-Baudouy Janine: An efficient and highly stereoselective α(1→4) glycosylation between two d-galacturonic acid ester derivatives. Tetrahetron Lett 1997, 38, 241. <http://dx.doi.org/10.1016/S0040-4039(96)02308-8>
  • Robina Inmaculada, López-Barba Eugenia, Jiménez-Barbero Jesús, Martín-Pastor Manuel, Fuentes José: Synthesis and conformational analysis of a lipotetrasaccharide related to the nodulation factor of Rhizobium bacteria. Tet Asymm 1997, 8, 1207. <http://dx.doi.org/10.1016/S0957-4166(97)00108-0>
  • Streicher Hansjörg, Reiner Martin, Schmidt Richard R.: Synthesis and Reactions of C-Hetaryl Substituted Ketoses. J Carbohydr Chem 1997, 16, 277. <http://dx.doi.org/10.1080/07328309708006530>
  • Streicher Hansjörg, Geyer Armin, Schmidt Richard R.: C-Disaccharides of Ketoses. Chem Eur J 1996, 2, 502. <http://dx.doi.org/10.1002/chem.19960020508>
  • Boons Geert-Jan: Strategies in Oligosaccharide Synthesis. Tetrahedron 1996, 52, 1095. <http://dx.doi.org/10.1016/0040-4020(95)00897-7>
  • Zhu Xiao Xiang, Ping Yu Ding, Cai Meng Shen: Synthesis of tetrasaccharides as possible metastatic inhibitors. Carbohydrates Research 1996, 296, 229. <http://dx.doi.org/10.1016/S0008-6215(96)00244-3>
  • Bassily Rafik W.: Synthesis and NMR Spectroscopic Studies of Trichloroacetimidate Lactosyl Donor. Spec Lett 1996, 29, 497. <http://dx.doi.org/10.1080/00387019608006666>
  • Robina Inmaculada, López-Barba Eugenia, Fuentes José: Synthesis of Glycosyl Acceptors by Regioselective Benzylations of a 2-Deoxy-2-phthalimido-D-glucoside. Synth Common 1996, 26, 2847. <http://dx.doi.org/10.1080/00397919608005219>
  • Li Zhong-Jun, Huang He-Qing, Cai Meng-Shen: Studies on Glycosides XVI. The Use of Mannosyl Trichloroacetate in the Synthesis of α-Mannosides and Related Oligosaccharides. J Carbohydr Chem 1996, 15, 501. <http://dx.doi.org/10.1080/07328309608005669>
  • Stahl W., Sprengard U., Kretzschmar G., Schmidt D. W., Kunz H.: Synthesis of Sulfated Lex-Trisaccharides. J Prakt Chem 1995, 337, 441. <http://dx.doi.org/10.1002/prac.19953370196>
  • Macindoe Wallace M., Ijima Hiroyuki, Nakahara Yoshiaki, Ogawa Tomoya: Stereoselective synthesis of a blood group A type glycopeptide present in human blood mucin. Carbohydrates Research 1995, 269, 227. <http://dx.doi.org/10.1016/0008-6215(94)00362-J>
  • Li Pan, Sun Lihong, Landry Donald W., Zhao Kang: Synthesis of 1-thioglycosides. Carbohydrates Research 1995, 275, 179. <http://dx.doi.org/10.1016/0008-6215(95)00021-K>
  • Mereyala Hari Babu, Guntha Sreenivasulu: Stereoselective synthesis of rare (D and L) mono and disaccharides of 5-deoxy hexofuranosiduronic acids by a facile intramolecular rearrangement of hemiacetal heptanolactone alcohols. Tetrahedron 1995, 51, 1741. <http://dx.doi.org/10.1016/0040-4020(94)01047-4>
  • Perrin Charles L.: Reverse anomeric effect: fact or fiction?. Tetrahedron 1995, 51, 11901. <http://dx.doi.org/10.1016/0040-4020(95)00560-U>
  • DeNinno Michael P., Etienne John B., Duplantier Kimberly C.: A method for the selective reduction of carbohydrate 4,6-O-benzylidene acetals. Tetrahetron Lett 1995, 36, 669. <http://dx.doi.org/10.1016/0040-4039(94)02348-F>
  • Sinou Denis, Frappa Isabelle, Lhoste Paul, Porwanski Stanislaw, Kryczka Boguslaw: Stereoselective palladium(0)-mediated synthesis of 1,4-disaccharides. Tetrahetron Lett 1995, 36, 1251. <http://dx.doi.org/10.1016/0040-4039(94)02480-Y>
  • Zhang Hong, Wang Yali, Voelter Wolfgang: A new strategy for the synthesis of the nephritogenoside trisaccharide unit using phenylsulfenyl donors. Tetrahetron Lett 1995, 36, 1243. <http://dx.doi.org/10.1016/0040-4039(94)02486-U>
  • Wang Hui, Sun Lihong, Glazebnik Serge, Zhao Kang: Peralkylation of saccharides under aqueous conditions. Tetrahetron Lett 1995, 36, 2953. <http://dx.doi.org/10.1016/0040-4039(95)00446-J>
  • Huchel Ursula, Schmidt Christoph, Schmidt Richard R.: Direct anomeric O-arylation and O-hetarylation of glucose - electron deficient aromatic and hetaromatic compounds in aryl and hetaryl glycoside synthesis. Tetrahetron Lett 1995, 36, 9457. <http://dx.doi.org/10.1016/0040-4039(95)02034-9>
  • Mao Jianmin, Chen Hongming, Zhang Jian, Cai Mengshen: Studies on Glycosides XIV. Stereoselectivity and Reactivity of New C1 Leaving Group Trichloroacetoxyl in Glycosylation Reaction. Synth Common 1995, 25, 1563. <http://dx.doi.org/10.1080/00397919508011769>
  • Kaji Eisuke, Lichtenthaler Frieder W., Osa Yumiko, Zen Shonosuke: A Novel, Readily Accessible Lactosaminyl Donor: N-Trichloroethoxycarbonyl-hexa-O-benzoyl-.BETA.-D-lactosaminyl Fluoride. Bull Chem Soc Jpn 1995, 68, 1172. <http://dx.doi.org/10.1246/bcsj.68.1172>
  • Stahl Wilhelm, Sprengard Ulrich, Kretzschmar Gerhard, Kunz Horst: Synthese von Desoxy-Sialyl-Lewisx-Analoga, potentiellen Selectin-Antagonisten. Angew Chem 1994, 106, 2186. <http://dx.doi.org/10.1002/ange.19941062025>
  • Frische Klaus, Schmidt Richard R.: Glycal-1-ylmethylphosphonates – precursors of glycosyltransferase inhibitors. Liebigs Ann Chem 1994, 1994, 297. <http://dx.doi.org/10.1002/jlac.199419940312>
  • Ziegler Thomas, Herold Gerhard: Preparation of Diastereomeric 3,4-O-Pyruvate Acetal-ContainingD-Galactopyranose Derivatives, Structural Assignment and Use for Oligosaccharide Synthesis. Liebigs Ann Chem 1994, 1994, 859. <http://dx.doi.org/10.1002/jlac.199419940903>
  • Dietrich Hansjörg, Schmidt Richard R.: Synthesis of Carbon-BridgedC-Lactose and Derivatives. Liebigs Ann Chem 1994, 1994, 975. <http://dx.doi.org/10.1002/jlac.199419941004>
  • Sun Lihong, Li Pan, Zhao Kang: Stabilization of glycosyl sulfonium ions for stereoselective O-glycosylation. Tetrahetron Lett 1994, 35, 7147. <http://dx.doi.org/10.1016/0040-4039(94)85346-0>
  • Magnusson Göran: Synthesis of glycosphingolipids and corresponding neoglycolipids. Adv Drug Delivery Rev 1994, 13, 267. <http://dx.doi.org/10.1016/0169-409X(94)90015-9>
  • Khan Riaz, Konowicz Paul A., Gardossi Lucia, Matulovà Maria, Paoletti Sergio: Chemical regioselective hydrolysis of peracetylated reducing disaccharides, specifically at the anomeric centre: Intermediates for the synthesis of oligosaccharides. Tetrahetron Lett 1994, 35, 4247. <http://dx.doi.org/10.1016/S0040-4039(00)73164-9>
  • Müller Thomas, Schneider Regine, Schmidt Richard R.: Utility of glycosyl phosphites as glycosyl donors-fructofuranosyl and 2-deoxyhexopyranosyl phosphites in glycoside bond formation. Tetrahetron Lett 1994, 35, 4763. <http://dx.doi.org/10.1016/S0040-4039(00)76961-9>
  • Ragan John A., Cooper Kelvin: Synthesis of a galactose-fucose disaccharide mimic of sialyl Lewis X. Biorg Med Chem Lett 1994, 4, 2563. <http://dx.doi.org/10.1016/S0960-894X(01)80284-5>
  • Martin Thomas J., Braun Heik, Schmidt Richard R.: A convenient synthesis of nucleoside monophosphate-N-acetylneuraminic acids (NMP-Neu5AC). biorg med chem 1994, 2, 1203. <http://dx.doi.org/10.1016/S0968-0896(00)82071-4>
  • Lafont Dominique, Boullanger Paul, Fenet Bernard: Reacttvite Comparee de Divers Accepteurs de la d-Glucosamine lors de la Synthese de Precurseurs du Chitobiose. J Carbohydr Chem 1994, 13, 565. <http://dx.doi.org/10.1080/07328309408011665>
  • Lamberth Clemens, Nagy Jon O., Kasper Cornelia, Bednarski Mark D.: Synthesis of Selectively Protected Chitobiose and Chitotriose Derivatives from one Precursor. Versatile Building Blocks for Oligosaccharide Synthesis. J Carbohydr Chem 1994, 13, 819. <http://dx.doi.org/10.1080/07328309408011682>
  • Klotz Wolfgang, Schmidt Richard R.: Anomeric O-Alkylation of O-Acetyl-Protected Sugars. J Carbohydr Chem 1994, 13, 1093. <http://dx.doi.org/10.1080/07328309408011851>
  • Klotz Wolfgang, Schmidt Richard R.: AnomericO-alkylation, 11. AnomericO-Alkylation ofO-Unprotected Hexoses and Pentoses – Convenient Synthesis of Decyl, Benzyl, and Allyl Glycosides. Liebigs Ann Chem 1993, 1993, 683. <http://dx.doi.org/10.1002/jlac.1993199301110>
  • Greilich Ulrike, Zimmermann Peter, Jung Karl-Heinz, Schmidt Richard R.: Glycosyl Imidates, 62. – Synthesis of the Heptasaccharide Moiety of Ganglioside BGM1. Liebigs Ann Chem 1993, 1993, 859. <http://dx.doi.org/10.1002/jlac.1993199301136>
  • Dean Barbara, Oguchi Hisao, Cai Shaopei, Otsuji Eigo, Tashiro Kazuhiro, Hakomori Sen-itiroh, Toyokuni Tatsushi: Synthesis of multivalent β-lactosyl clusters as potential tumor metastasis inhibitors. Carbohydrates Research 1993, 245, 175. <http://dx.doi.org/10.1016/0008-6215(93)80071-L>
  • Kinzy Willy, Löw Alexandra: Kohlenhydrat-Bausteine zum Aufbau Tumor-assoziierter Antigene. Synthese von Lewis Y-Determinanten. Carbohydrates Research 1993, 245, 193. <http://dx.doi.org/10.1016/0008-6215(93)80072-M>
  • Rembold Hansjör, Schmidt Richard R.: Synthesis of Kdo-α-glycosides of lipid A derivatives. Carbohydrates Research 1993, 246, 137. <http://dx.doi.org/10.1016/0008-6215(93)84029-6>
  • Ekberg Tomas, Magnusson Göran: Synthesis of 3′- and 4′-deoxyfluorolactose and its Me3SiCH2CH2 and ceramide derivatives. Carbohydrates Research 1993, 249, 117. <http://dx.doi.org/10.1016/0008-6215(93)84065-E>
  • Toepfer Alexander, Schmidt Richard R.: A convenient synthesis of N-acetyllactosamine derivatives from lactal. Carbohydrates Research 1993, 247, 159. <http://dx.doi.org/10.1016/0008-6215(93)84249-6>
  • Möller Uwe, Hobert Kurt, Donnerstrag Astrid, Wagner Petra, Müller Dietrich, Fehlhaber Hans-Wolfram, Markus Astrid, Welzel Peter: Moenomycin A - Structure-activity relations synthesis of the D-galacturonamide analogue of the smallest antibiotically active degradation product of moenomycin A. Tetrahedron 1993, 49, 1635. <http://dx.doi.org/10.1016/S0040-4020(01)80351-3>
  • Ager David J., East Michael B.: The synthesis of carbohydrate derivatives from acyclic precursors. Tetrahedron 1993, 49, 5683. <http://dx.doi.org/10.1016/S0040-4020(01)87942-4>
  • Martin Thomas J., Schmidt Richard R.: Convenient chemical synthesis of CMP-N-acetylneuraminate (CMP-Neu-5-Ac). Tetrahetron Lett 1993, 34, 1765. <http://dx.doi.org/10.1016/S0040-4039(00)60773-6>
  • Khan Riaz, Gropen Line, Konowicz Paul A., Matulovà Maria, Paoletti Sergio: Enzymic regioselective hydrolysis of peracetylated reducing disaccharides, specifically at the anomeric centre: Intermediates for the synthesis of oligosaccharides. Tetrahetron Lett 1993, 34, 7767. <http://dx.doi.org/10.1016/S0040-4039(00)61561-7>
  • Behrendt Michael E., Schmidt Richard R.: Leaving group based intramolecular glycoside bond formation. Tetrahetron Lett 1993, 34, 6733. <http://dx.doi.org/10.1016/S0040-4039(00)61687-8>
  • Schmidt Richard R., Frische Klaus: A new galactosyl transferase inhibitor. Biorg Med Chem Lett 1993, 3, 1747. <http://dx.doi.org/10.1016/S0960-894X(00)80055-4>
  • Inanaga Junji, Yokoyama Yasuo, Hanamoto Takeshi: Utility of 3,4-Dimethoxybenzyl(DMPM) Glycosides. A New Glycosylation Triggered by 2,3-Dichloro-5,6-dicyano-p-benzoquinone(DDQ) Oxidation. Chem Lett 1993, 85. <http://dx.doi.org/10.1246/cl.1993.85>
  • Plewe Michael, Sandhoff Konrad, Schmidt Richard R.: Synthesis of 4-Epoxy-4-c-methyleneglycosylceramides, Potential Glycosyltransferase Inhibitors. Liebigs Ann Chem 1992, 1992, 699. <http://dx.doi.org/10.1002/jlac.1992199201118>
  • Jiang Zi-Hua, Schmidt Richard R.: Glycosyl Imidates, 56. Synthesis of the Hexasaccharide Moiety of Pectinioside E. Liebigs Ann Chem 1992, 1992, 975. <http://dx.doi.org/10.1002/jlac.1992199201160>
  • Qiu Dongxu, Schmidt Richard R.: Glycosyl Imidates, 52. Synthesis of Globotriaosylceramide (Gb3) and Isoglobotriaosylceramide (isoGb3). Liebigs Ann Chem 1992, 1992, 217. <http://dx.doi.org/10.1002/jlac.199219920140>
  • Tsvetkov Yury E., Klotz Wolfgang, Schmidt Richard R.: AnomericO-Alkylation, 9. Disaccharide Synthesis via AnomericO-Alkylation. Liebigs Ann Chem 1992, 1992, 371. <http://dx.doi.org/10.1002/jlac.199219920165>
  • Termin Andreas, Schmidt Richard R.: Glycosylimidates, 54. Synthesis of the GlcNAcβ(1→4)MurNAcβ(1→4)GlcNAcβ(1→4)MurNAc tetrasaccharide of bacterial peptidoglycan. Liebigs Ann Chem 1992, 1992, 527. <http://dx.doi.org/10.1002/jlac.199219920191>
  • Plewe Michael, Sandhoff Konrad, Schmidt Richard R.: Synthesis of 4-C-methyl analogues of glucosylceramide. Carbohydrates Research 1992, 235, 151. <http://dx.doi.org/10.1016/0008-6215(92)80085-F>
  • Zapata Amparo, Martín-Lomas Manuel: Building blocks for the synthesis of glycosyl-myo-inositols involved in the insulin intracellular signalling process. Carbohydrates Research 1992, 234, 93. <http://dx.doi.org/10.1016/0008-6215(92)85041-W>
  • Toepfer Alexander, Schmidt Richard R.: An efficient synthesis of the Lewis X (Lex) antigen family. Tetrahetron Lett 1992, 33, 5161. <http://dx.doi.org/10.1016/S0040-4039(00)79122-2>
  • Koto Shinkiti, Morishima Naohiko, Shichi Sonoko, Haigoh Hisamitsu, Hirooka Motoko, Okamoto Mitsuko, Higuchi Takashi, Shimizu Koichi, Hashimoto Yosuke, Irisawa Terumi: Dehydrative Glycosylation Using Heptabenzyl Derivatives of Glucobioses and Lactose. Bull Chem Soc Jpn 1992, 65, 3257. <http://dx.doi.org/10.1246/bcsj.65.3257>
  • Fukase Koichi, Hase Sumihiro, Ikenaka Tokuji, Kusumoto Shoichi: Synthesis of New Serine-Linked Oligosaccharides in Blood-Clotting Factors VII and IX and Protein Z. The Syntheses of O-.ALPHA.-D-Xylopyranosyl-(1.RAR.3)-D-glucopyranose, O-.ALPHA.-D-Xylopyranosyl-(1.RAR.3)-O-.ALPHA.-D-xylopyranosyl-(1.RAR.3)-D-glucopyranose, and Their Conjugates with Serine. Bull Chem Soc Jpn 1992, 65, 436. <http://dx.doi.org/10.1246/bcsj.65.436>
  • Schmidt Richard R., Dietrich Hansjörg: Aminosubstituierteβ-Benzyl-C-glycoside, neuartigeβ-Glycosidase-Inhibitoren. Angew Chem 1991, 103, 1348. <http://dx.doi.org/10.1002/ange.19911031016>
  • Schaubach Regine, Hemberger Jürgen, Kinzy Willy: Tumor-associated antigen synthesis synthesis of the gal-α-(1→3)-gal-β-(1→4)-GlcNAc epitope a specific determinant for metastatic progression?. Liebigs Ann Chem 1991, 1991, 607. <http://dx.doi.org/10.1002/jlac.1991199101113>
  • Kottenhahn Matthias, Kessler Horst: Synthese von 2-Desoxy-α-O-glycopeptiden mit demN-Iodsuccinimid-(NIS-) Verfahren. Liebigs Ann Chem 1991, 1991, 727. <http://dx.doi.org/10.1002/jlac.1991199101127>
  • Bär Thomas, Schmidt Richard R.: Synthesis of β-lactosyl 1-thioceramide. Liebigs Ann Chem 1991, 1991, 185. <http://dx.doi.org/10.1002/jlac.199119910133>
  • Bommer René, Kinzy Willy, Schmidt Richard R.: Glycosyl imidates. 49. Synthesis of the octasaccharide moiety of the dimeric Lex antigen. Liebigs Ann Chem 1991, 1991, 425. <http://dx.doi.org/10.1002/jlac.199119910178>
  • Koide Kazunori, Ohno Masaji, Kobayashi Susumu: A new glycosylation reaction based on a “remote activation concept”: glycosyl 2-pyridinecarboxylate as a novel glycosyl donor. Tetrahetron Lett 1991, 32, 7065. <http://dx.doi.org/10.1016/0040-4039(91)85041-3>
  • Schmidt Richard R., Toepfer Alexander: Glycosylation with highly reactive glycosyl donors: efficiency of the inverse procedure. Tetrahetron Lett 1991, 32, 3353. <http://dx.doi.org/10.1016/S0040-4039(00)92704-7>
  • Toepfer Alexander, Schmidt Richard R.: Muramic acid derivatives as glycosyl donors for the synthesis of muramyl-containing glycosphingolipids and fatty acids. Carbohydrates Research 1990, 202, 193. <http://dx.doi.org/10.1016/0008-6215(90)84080-E>
  • Urban Frank J., Moore Bernard S., Breitenbach Ralph: Synthesis of tigogenyl β-O-cellobioside heptaacetate and glycoside tetraacetate via Schmidt's trichloroacetimidate method; some new observatons. Tetrahetron Lett 1990, 31, 4421. <http://dx.doi.org/10.1016/S0040-4039(00)97637-8>
  • Zimmermann Peter, Greilich Ulrike, Schmidt Richard R.: Total synthesis of a hexaosyl ceramide glycolipid acting as a receptor for macrophage migration inhibition-factor. Tetrahetron Lett 1990, 31, 1849. <http://dx.doi.org/10.1016/S0040-4039(00)98802-6>
  • Singh Narrinder P., Giannis Athanassios, Henk Elfi, Kolter Thomas, Sandhoff Konrad, Schmidt Richard R.: Synthesis of 2-Carboxy-Substituted Sphingosine Derivatives. J Carbohydr Chem 1990, 9, 543. <http://dx.doi.org/10.1080/07328309008543852>