2-C-branched glycosides from 2'-carbonylalkyl 2-O-Ms(Ts)-C-glycosides.: A tandem SN2-SN2 reaction via 1,2-cyclopropanated sugars

被引：32
|
作者：
Shao, HW
Ekthawatchai, S
Wu, SH
Zou, W
机构：
[1] Natl Res Council Canada, Inst Biol Sci, Ottawa, ON K1A 0R6, Canada
[2] Acad Sinica, Inst Biol Chem, Taipei 115, Taiwan
来源：
ORGANIC LETTERS | 2004年 / 6卷 / 20期
关键词：
D O I：
10.1021/ol0486627
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Under basic conditions, 2'-aldehydo (acetonyl) 2-O-Ms(Ts)-alpha-C-glycosides undergo an intramolecular S(N)2 reaction to form 1,2-cyclopropanated sugars, which react with nucleophiles (alcohols, thiols, and azide) at the anomeric carbon to give 2-C-branched glycosides. By way of contrast, the 1,2-cyclopropanes derived from 2'-ketones only react with thiols to give 2-C-branched thioglycosides.
引用
收藏
页码：3497 / 3499
页数：3
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