Glycosylation using glucopyranosyl fluorides and silicon-based catalysts. Solvent dependency of the stereoselection

作者: S. Hashimoto , M. Hayashi , R. Noyori

DOI: 10.1016/S0040-4039(01)80163-5

关键词: Steric effectsSolvent effectsSolventStereoselectivityChemistryOrganic chemistryAcetonitrileSilicon basedCatalysisGlycosylation

摘要: Abstract The title glycosylation method is economical and operationally simple. steric course highly influenced by the nature of reaction media.

参考文章(17)
Lutz-F. Tietze, Roland Fischer, Stereoselektive synthese von α-glucosiden mit 1,1′ -diacetal-struktur Tetrahedron Letters. ,vol. 22, pp. 3239- 3242 ,(1981) , 10.1016/S0040-4039(01)81872-4
Shinkiti Koto, Naohiko Morishima, Shonosuke Zen, Glucosidation of Tetra-O-benzyl-α-D-glucose with Chlorosilane and Silver Sulfonate Bulletin of the Chemical Society of Japan. ,vol. 52, pp. 784- 788 ,(1979) , 10.1246/BCSJ.52.784
Günter Wulff, Ulrich Schröder, Jürgen Wilchelhaus, On the stereochemical control of glycosylation reactions by the addition of tetrahydrofuran Carbohydrate Research. ,vol. 72, pp. 280- 284 ,(1979) , 10.1016/S0008-6215(00)83950-6
Lutz-F Tietze, Poland Fischer, Hans-Joachim Guder, Einfache und stereoselektive synthese von α- und β-phenylglykosiden Tetrahedron Letters. ,vol. 23, pp. 4661- 4664 ,(1982) , 10.1016/S0040-4039(00)85681-6
S. P. Seitz, D. P. Papahatjis, K. C. Nicolaou, A mild and general method for the synthesis of 0-glycosides Journal of the American Chemical Society. ,vol. 105, pp. 2430- 2434 ,(1983) , 10.1021/JA00346A053
Hans Paulsen, Advances in Selective Chemical Syntheses of Complex Oligosaccharides Angewandte Chemie. ,vol. 21, pp. 155- 173 ,(1982) , 10.1002/ANIE.198201553
Günter Wulff, Gerbard Röhle, Results and Problems of O-Glycoside Synthesis Angewandte Chemie. ,vol. 13, pp. 157- 170 ,(1974) , 10.1002/ANIE.197401571
Richard R. Schmidt, Josef Michel, Facile Synthesis of α‐ and β‐O‐Glycosyl Imidates; Preparation of Glycosides and Disaccharides Angewandte Chemie. ,vol. 19, pp. 731- 732 ,(1980) , 10.1002/ANIE.198007311