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
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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