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Pure Appl. Chem., 1978, Vol. 50, No. 11-12, pp. 1437-1452

http://dx.doi.org/10.1351/pac197850111437

Recent advances in glycosylation reactions

P. Sinaÿ

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  • Talisman Ian Jamie, Kumar Vineet, Razzaghy Jacqueline, Malhotra Sanjay V.: O-Glycosidation reactions promoted by in situ generated silver N-heterocyclic carbenes in ionic liquids. Carbohydrates Research 2011, 346, 883. <http://dx.doi.org/10.1016/j.carres.2011.03.007>
  • Kaeothip Sophon, Akins Steven J., Demchenko Alexei V.: On the stereoselectivity of glycosidation of thiocyanates, thioimidates, and thioglycosides. Carbohydrates Research 2010, 345, 2146. <http://dx.doi.org/10.1016/j.carres.2010.08.003>
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  • Mesa Juan A., Tacoronte Juan E., García Ernesto, Leyva Jorge: An Easy Regio- and Stereoselective Synthesis of a Versatile Trisaccharide Precursor for Synthetic Carbohydrate Based Vaccines. Collect Czech Chem Commun 2007, 72, 411. <http://dx.doi.org/10.1135/cccc20070411>
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  • Bindschädler Pascal, Noti Christian, Castagnetti Eva, Seeberger Peter H.: Synthesis of a Potential 10E4 Tetrasaccharide Antigen Involved in Scrapie Pathogenesis. HCA 2006, 89, 2591. <http://dx.doi.org/10.1002/hlca.200690234>
  • Fraser-Reid Bert, Lu Jun, Jayaprakash K.N., López J. Cristóbal: Synthesis of a 28-mer oligosaccharide core of Mycobacterial lipoarabinomannan (LAM) requires only two n-pentenyl orthoester progenitors. Tet Asymm 2006, 17, 2449. <http://dx.doi.org/10.1016/j.tetasy.2006.09.008>
  • Ikuta Akiko, Tanimoto Toshiko, Koizumi Kyoko: Efficient Chemical Syntheses of Branched Cyclomalto‐Oligosaccharides Using the Trichloroacetimidate Method. J Carbohydr Chem 2003, 22, 297. <http://dx.doi.org/10.1081/CAR-120023472>
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  • Zhang Guang-tao, Guo Zhong-wu, Hui Yong-zheng: A Facile Regioselective 1,6-O-Diacetylation Method of Methyl-Glycopyranosides and Their Dimethyl Phosphonates. Synth Common 1997, 27, 1907. <http://dx.doi.org/10.1080/00397919708006792>
  • Boons Geert-Jan: Strategies in Oligosaccharide Synthesis. Tetrahedron 1996, 52, 1095. <http://dx.doi.org/10.1016/0040-4020(95)00897-7>
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  • Nishimura Takeshi, Nakatsubo Fumiaki: First synthesis of cellooctaose by a convergent synthetic method. Carbohydrates Research 1996, 294, 53. <http://dx.doi.org/10.1016/S0008-6215(96)90617-5>
  • Nishimura Takeshi, Nakatsubo Fumiaki: First stepwise synthesis of cellulose analogs. Tetrahetron Lett 1996, 37, 9215. <http://dx.doi.org/10.1016/S0040-4039(96)02186-7>
  • Pet[otilde] Csaba, Batta Gyula, Györgydeák Zoltán, Sztaricskai Ferenc: Glycoside Synthesis with Anomeric 1-N-Glycobiosyl-1,2,3-triazoles1. J Carbohydr Chem 1996, 15, 465. <http://dx.doi.org/10.1080/07328309608005667>
  • Dasgupta Falguni, Anderson Laurens: Efficient preparation of allyl 2,3,6,2′,3′,6′-hexa-O-benzyl-β-lactoside and its use as a glycosyl acceptor for chain extension at O-4′. Carbohydrates Research 1994, 264, 155. <http://dx.doi.org/10.1016/0008-6215(94)00189-8>
  • Koeman A. W., Meissner Johannes W. G., van Ritter Hendrik R. P., Kamerling Johannis P., Vliegenthart Johannes F. G.: Synthesis of Structural Elements of the Capsular Polysaccharide of Streptococcus Pneumoniae Type 14. J Carbohydr Chem 1994, 13, 1. <http://dx.doi.org/10.1080/07328309408009174>
  • Maloisel Jean-Luc, Vasella Andrea: Synthesis ofN-Acetylallosamine-Derived Disaccharides. HCA 1992, 75, 1491. <http://dx.doi.org/10.1002/hlca.19920750505>
  • Wessel Hans Peter, Englert Gerhard, Stangier Peter: α-D-Glycosyl-Substituted α,α-D-Trehaloses with (1 → 4)-Linkage: Syntheses and NMR Investigations. HCA 1991, 74, 682. <http://dx.doi.org/10.1002/hlca.19910740403>
  • Toshima Kazunobu, Nozaki Yuko, Tatsuta Kuniaki: Highly stereoselective glycosylation by conformational assistance of glycosyl donor. Tetrahetron Lett 1991, 32, 6887. <http://dx.doi.org/10.1016/0040-4039(91)80435-9>
  • Toshima Kazunobu, Mukaiyama Satsuki, Yoshida Takehito, Tamai Tetsuro, Tatsuta Kuniaki: Application of efficient glycosylation of 2,6-anhydro-2-thio sugar to the total synthesis of erythromycin A. Tetrahetron Lett 1991, 32, 6155. <http://dx.doi.org/10.1016/0040-4039(91)80777-4>
  • Barton Derek H.R., Jaszberenyi Joseph Cs., Theodorakis Emmanouil A.: O-Sulfinylation of alcohols with methanesulfonyl cyanide or p-toluenesulfonyl cyanide. Tetrahedron 1991, 47, 9167. <http://dx.doi.org/10.1016/S0040-4020(01)96204-0>
  • Dauben William G., Köhler Peter: High-pressure glycosylations of unreactive alcohols and the formation of N-glycosyl collidinium salts. Carbohydrates Research 1990, 203, 47. <http://dx.doi.org/10.1016/0008-6215(90)80044-4>
  • Glushka John N., Perlin Arthur S.: Formation of disaccharides related to heparin and heparan sulfate by chemical modification of maltose. Carbohydrates Research 1990, 205, 305. <http://dx.doi.org/10.1016/0008-6215(90)80149-W>
  • Toshima Kazunobu, Mukaiyama Satsuki, Ishiyama Takashi, Tatsuta Kuniaki: The use of 2,6-anhydro-2-thio sugar for a highly stereocontrolled glycosylation: A novel strategy for synthesis of 2,6-dideoxy-α-glycosides. Tetrahetron Lett 1990, 31, 3339. <http://dx.doi.org/10.1016/S0040-4039(00)89059-0>
  • Nifant'ev Nikolay E., Backinowsky Leon V., Kochetkov Nikolay K.: Synthesis of derivatives of 2-amino-2-deoxy-4-O-(α- and β-d-galactopyranosyl)-d-glucose. Carbohydrates Research 1988, 174, 61. <http://dx.doi.org/10.1016/0008-6215(88)85081-X>
  • Fügedi Péter: Synthesis of 4-O-(α-L-Rhamnopyranosyl-D-Glucopyranuronic Acid. J Carbohydr Chem 1987, 6, 377. <http://dx.doi.org/10.1080/07328308708057927>
  • Schmidt Richard R.: Neue Methoden zur Glycosid- und Oligosaccharidsynthese – gibt es Alternativen zur Koenigs-Knorr-Methode?. Angew Chem 1986, 98, 213. <http://dx.doi.org/10.1002/ange.19860980305>
  • Schmidt Richard R.: New Methods for the Synthesis of Glycosides and Oligosaccharides—Are There Alternatives to the Koenigs-Knorr Method? [New Synthetic Methods (56)]. Angew Chem Int Ed Engl 1986, 25, 212. <http://dx.doi.org/10.1002/anie.198602121>
  • Rathore Hargovind, Hashimoto Toshihiro, Igarashi Kikuo, Nukaya Haruo, Fullerton Dwight S.: Cardiac glycosides: 5. Stereoselective syntheses of digitoxigenin α-D, β-D, α-L, and β-L-glucosides. Tetrahedron 1985, 41, 5427. <http://dx.doi.org/10.1016/S0040-4020(01)91342-0>
  • Schmidt Richard R., Michel Josef: O-(α-D-Glucopyranosyl)trichloroacetimidate as a Glucosyl Donor. J Carbohydr Chem 1985, 4, 141. <http://dx.doi.org/10.1080/07328308508058829>
  • Takeo Ken'ichi, Shinmitsu Kazuyuki: A convenient synthesis of 6′-C-substituted β-maltose heptaacetates and of panose. Carbohydrates Research 1984, 133, 135. <http://dx.doi.org/10.1016/0008-6215(84)85189-7>
  • Wessel Hans-Peter, Iversen Tommy, Bundle David R.: Synthesis of the trisaccharide moiety of gangliotriosylceramide (asialo GM2). Carbohydrates Research 1984, 130, 5. <http://dx.doi.org/10.1016/0008-6215(84)85266-0>
  • Takeo Ken'ichi, Okushio Kazuo, Fukuyama Katsumi, Kuge Takashi: Synthesis of cellobiose, cellotriose, cellotetraose, and lactose. Carbohydrate Research 1983, 121, 163. <http://dx.doi.org/10.1016/0008-6215(83)84014-2>
  • Bovin Nikolai V., Zurabyan Sergei É., Khorlin Anatoly Ya.: Stereoselectivity of glycosylation with derivatives of 2-azido-2-deoxy-d-galactopyranose. The synthesis of a determinant oligosaccharide related to blood-group a (type 1). Carbohydrates Research 1983, 112, 23. <http://dx.doi.org/10.1016/0008-6215(83)88263-9>
  • Sadeh Shoshana, Warren Christopher D., Jeanloz Roger W.: 2-O-Acetyl-3,4-di-O-benzyl-6-O-(tert-butyldiphenylsilyl)-d-glucopyranosyl chloride as a d-glycosyl donor. Carbohydrates Research 1983, 123, 73. <http://dx.doi.org/10.1016/0008-6215(83)88382-7>
  • Paulsen Hans: Advances in Selective Chemical Syntheses of Complex Oligosaccharides. Angew Chem Int Ed Engl 1982, 21, 155. <http://dx.doi.org/10.1002/anie.198201553>
  • Hindsgaul Ole, Norberg Thomas, Le Pendu Jacques, Lemieux Raymond U.: Synthesis of type 2 human blood-group antigenic determinants. The H, X, and Y haptens and variations of the H type 2 determinant as probes for the combining site of the lectin I of Ulex europaeus. Carbohydrates Research 1982, 109, 109. <http://dx.doi.org/10.1016/0008-6215(82)84034-2>
  • Paulsen Hans, Bünsch Almuth: Synthese der pentasaccharid-kette des forssman-antigens. Carbohydrates Research 1982, 100, 143. <http://dx.doi.org/10.1016/S0008-6215(00)81032-0>
  • Zollo Paul Amvam, Sinaÿ Pierre, Milat Marie-Louise: Application of the imidate procedure to α-d-galactosyltion. Carbohydrates Research 1982, 100, 263. <http://dx.doi.org/10.1016/S0008-6215(00)81040-X>
  • Paulsen Hans, Jacquinet Jean-Claude, Rust Wolfgang: Synthese von oligosaccharid-determinanten mit amid-spacer vom typ des t-antigens. Carbohydrates Research 1982, 104, 195. <http://dx.doi.org/10.1016/S0008-6215(00)82583-5>
  • Paulsen Hans, Kolář Čenêk: Bausteine von Oligosacchariden, XX1) Synthese der Oligosaccharid-Determinanten der Blutgruppensubstanzen der Type 2 des ABH-Systems. Diskussion der α-Glycosid-Synthese. Chem Ber 1981, 114, 306. <http://dx.doi.org/10.1002/cber.19811140134>
  • Boivin Jean, Monneret Claude, Païs Mary: Synthese d'un disaccharide, constituant naturel d'anthracyclines antibiotiques et antitumorales. Tetrahetron Lett 1980, 21, 2413. <http://dx.doi.org/10.1016/S0040-4039(00)93163-0>