Glycosylthiomethyl Chloride: A New Species for S-Neoglycoconjugate Synthesis. Synthesis of 1-N-Glycosylthiomethyl-1,2,3-triazoles
- 20 January 2004
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 69 (4) , 1081-1085
- https://doi.org/10.1021/jo035300o
Abstract
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.Keywords
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