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Pure Appl. Chem., 1997, Vol. 69, No. 3, pp. 459-464

http://dx.doi.org/10.1351/pac199769030459

Synthesis of oligosaccharide mimetics

P. Sinaÿ

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  • Delaunay Thierry, Poisson Thomas, Jubault Philippe, Pannecoucke Xavier: Stereoselective Access to β-C -Glycosamines by Nitro-Michael Addition of Organolithium Reagents. Eur. J. Org. Chem. 2014, n/a. <http://dx.doi.org/10.1002/ejoc.201402001>
  • Redon Sébastien, Wierzbicki Michel, Prunet Joëlle: A new oxa-Michael reaction and a gold-catalysed cyclisation en route to C-glycosides. Tetrahedron Letters 2013, 54, 2089. <http://dx.doi.org/10.1016/j.tetlet.2013.02.022>
  • Cobo Isidro, Matheu M. Isabel, Castillón Sergio, Boutureira Omar, Davis Benjamin G.: Phosphine-Free Suzuki–Miyaura Cross-Coupling in Aqueous Media Enables Access to 2-C-Aryl-Glycosides. Z Org Lett 2012, 14, 1728. <http://dx.doi.org/10.1021/ol3003139>
  • Li Boyu, Wang Gang, Li Zhongjun, Meng Xiangbao: InCl3-catalyzed synthesis of C-pyrrolyl glycosides via tandem condensation of aminosugars and 1,3-dicarbonyl compounds in water. Tetrahedron Letters 2011, 52, 3891. <http://dx.doi.org/10.1016/j.tetlet.2011.05.083>
  • Pasetto Paolo, Walczak Matthew C.: A Mitsunobu route to C-glycosides. Tetrahedron 2009, 65, 8468. <http://dx.doi.org/10.1016/j.tet.2009.08.024>
  • Nepogodiev Sergey A., Dedola Simone, Marmuse Laurence, de Oliveira Marcelo T., Field Robert A.: Synthesis of triazole-linked pseudo-starch fragments. Carbohydrates Research 2007, 342, 529. <http://dx.doi.org/10.1016/j.carres.2006.09.026>
  • García-Aparicio Víctor, Sollogoub Matthieu, Blériot Yves, Colliou Virginie, André Sabine, Asensio Juan L., Cañada F. Javier, Gabius Hans-Joachim, Sinaÿ Pierre, Jiménez-Barbero Jesús: The conformation of the C-glycosyl analogue of N-acetyl-lactosamine in the free state and bound to a toxic plant agglutinin and human adhesion/growth-regulatory galectin-1. Carbohydrates Research 2007, 342, 1918. <http://dx.doi.org/10.1016/j.carres.2007.02.034>
  • Yamamoto Yoshihiko, Saigoku Tomoaki, Nishiyama Hisao, Ohgai Takashige, Itoh Kenji: Selective synthesis of C-arylglycosides via Cp*RuCl-catalyzed partially intramolecular cyclotrimerizations of C-alkynylglycosides. Org Biomol Chem 2005, 3, 1768. <http://dx.doi.org/10.1039/b503258j>
  • Levoirier Eric, Canac Yves, Norsikian Stéphanie, Lubineau André: Indium-promoted Barbier-type allylations in aqueous media: a convenient approach to 4-C-branched monosaccharides and (1→4)-C-disaccharides. Carbohydrates Research 2004, 339, 2737. <http://dx.doi.org/10.1016/j.carres.2004.09.010>
  • Janes Erik, Dötz Karl Heinz: Organotransition metal modified sugars. J Organomet Chem 2003, 669, 1. <http://dx.doi.org/10.1016/S0022-328X(02)02160-5>
  • Peters Siegfried, Lichtenthaler Frieder W., Lindner Hans J.: A 2-C-fructosyl-propanone locked in a 2,7-dioxabicyclo[3.2.1]octane framework. Tet Asymm 2003, 14, 2475. <http://dx.doi.org/10.1016/S0957-4166(03)00501-9>
  • Ghosh Rina, Chakraborty Arijit, Maiti Dilip K.: In(OTf)3—A New Efficient Lewis Acid Catalyst for Stereoselective C-Glycosylation Reactions of Glycal Derivatives. Synth Common 2003, 33, 1623. <http://dx.doi.org/10.1081/SCC-120018923>
  • Hoffmann H. Martin R., Dunkel Ralf, Mentzel Matthias, Reuter Henning, Stark Christian B. W.: The Total Synthesis of C-Glycosides with Completely Resolved Seven-Carbon Backbone Polyol Stereochemistry: Stereochemical Correlations and Access toL-Configured and Other Rare Carbohydrates. Chem Eur J 2001, 7, 4771. <http://dx.doi.org/10.1002/1521-3765(20011119)7:22<4771::AID-CHEM4771>3.0.CO;2-J>
  • Vauzeilles Boris, Sinaÿ Pierre: Selective radical synthesis of β-C-disaccharides. Tetrahetron Lett 2001, 42, 7269. <http://dx.doi.org/10.1016/S0040-4039(01)01533-7>
  • Pham-Huu Duy-Phong, Petrušová Mária, BeMiller James N., Petruš Ladislav: The first synthesis of a nitromethylene-linked C-(1→2)-disaccharide. Tetrahetron Lett 1999, 40, 3053. <http://dx.doi.org/10.1016/S0040-4039(99)00363-9>
  • Gerber Patrick, Vogel Pierre: Total stereoselective syntheses of β-C-manno-pyranosides and of β-C(1→3)-linked disaccharides. Tetrahetron Lett 1999, 40, 3165. <http://dx.doi.org/10.1016/S0040-4039(99)00432-3>
  • Pasquarello Carla, Demange Raynald, Vogel Pierre: Synthesis of α-C(1→3)-mannopyranoside of N-acetylgalactosamine, a new β-galactosidase inhibitor. Biorg Med Chem Lett 1999, 9, 793. <http://dx.doi.org/10.1016/S0960-894X(99)00064-5>
  • Pietruszka Jörg: Faszinierende Organische Synthesechemie. Nachr Chem Tech Lab 1998, 46, 963. <http://dx.doi.org/10.1002/nadc.19980461015>
  • Du Yuguo, Linhardt Robert J., Vlahov Iontcho R.: Recent advances in stereoselective c-glycoside synthesis. Tetrahedron 1998, 54, 9913. <http://dx.doi.org/10.1016/S0040-4020(98)00405-0>
  • Belica Peter S., Franck Richard W.: Benzylic C-glycosides via the Ramberg-Backlund reaction. Tetrahetron Lett 1998, 39, 8225. <http://dx.doi.org/10.1016/S0040-4039(98)01881-4>
  • 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>