Glycosylthiomethyl chloride:: A new species for S-neoglycoconjugate synthesis.: Synthesis of 1-N-glycosylthiomethyl-1,2,3-triazoles

被引：40

作者：

Zhu, XM ^{[1
]}

Schmidt, RR ^{[1
]}

机构：

[1] Univ Konstanz, Fachbereich Chem, D-78457 Constance, Germany

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 69卷 / 04期

关键词：

D O I：

10.1021/jo035300o

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reaction of O-acyl-protected glycosylthiols with dichloromethane afforded readily glycosylthiomethyl chlorides, which gave with sodium azide the corresponding glycosylthiomethyl azides 17-22. Reaction of these azides with dicyclopentadiene as dipolarophile led to tandem 1,3-dipolar cycloaddition/retro-Diels-Alder reaction furnishing the parent 1-glycosylthiomethyl-1,2,3-triazoles 23-25. Reaction of azides with acetylene derivatives gave directly 1-glycosylthiomethyl-1,2,3-triazoles which are ring-substituted.

引用

页码：1081 / 1085

页数：5

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