Stereoselective 2-deoxy-β-O-glycoside synthesis based on remote activation of novel oxathiine donors

被引：0
|
作者：
Bartolozzi, A
Capozzi, G
Menichetti, S
Nativi, C
机构：
[1] Univ Florence, Dipartimento Chim Organ, CNR, Ctr Chim Composti Eterociclici, I-50121 Florence, Italy
[2] Univ Messina, Dipartimento Chim Organ & Biol, I-98166 Messina, Italy
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2001年 / 2001卷 / 11期
关键词：
cycloadditions; deoxysugars; desulfurizations; glycosidations;
D O I：
10.1002/1099-0690(200106)2001:11<2083::AID-EJOC2083>3.0.CO;2-T
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Stable glyco-fused 1,4-oxathiine derivatives, prepared by inverse electron-demand Diels-Alder reactions between suitable 1-glycals and 3-thioxopentane-2,4-dione, have been transformed into unusual glycosyl donors which, after "remote activation", react efficiently with glycosyl acceptors to afford 2-thio-beta -O-glycosides with total stereoselectivity. Several O-nucleophiles were successfully glycosylated. Reductive removal of sulfur transformed the 2-thio-beta -O-glycosides into the corresponding 2-deoxy-beta -O-glycosides without affecting the stereochemistry of the anomeric carbon atom.
引用
收藏
页码：2083 / 2090
页数：8
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