Unusual anomeric rearrangement of para-nitrobenzoylxanthate D-glycosides:: a new direct stereoselective access to a-thioglycosides from pyranose sugars

被引：8
作者：
Ané, A
Naud, S
Lacône, V
Vidot, S
Fournial, A
Kar, A
Pipelier, M
Dubreuil, D
机构：
[1] Univ Nantes, CNRS, Synth Organ Lab, UMR 6513,Fac Sci & Tech, F-44322 Nantes 3, France
[2] Fac Sci & Tech, Synth Organ Lab, Abidjan 22, Cote Ivoire
来源：
TETRAHEDRON | 2006年 / 62卷 / 20期
关键词：
stereoselective alpha-thioglycosylation; alpha-glycopyranoside thiols; alpha-galactoside thiol; thiolo-thiono rearrangement; alpha-thiogalactolipids;
D O I：
10.1016/j.tet.2006.03.024
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A mild and general procedure for the synthesis of alpha-thioglycosides from glycopyranoses is described. The method involves the treatment of pyranose reductive sugar with sodium hydride, carbon disulfide, and p-nitrobenzoyl chloride, as a key step, to yield p-nitrobenzoyl-alpha-D-thioglycopyranose intermediates with high stereoselectivity, in a one-pot-two-step process. The interest of the strategy highlights a direct stereoselective access to ether-protected 1-thiol-alpha-D-glycopyranose derivatives (Gal, Glc, and Man) from pyranoses in the absence of anomeric 'Lewis acid' promoters. (c) 2006 Elsevier Ltd. All rights reserved.
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页码：4784 / 4794
页数：11
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