来自2'-羰基烷基2-O-甲磺酸酯（对甲苯磺酸酯）-C-糖苷的2-C-支链糖苷。通过1,2-环丙烷化糖的串联SN2-SN2反应。

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

作者信息

Shao Huawu, Ekthawatchai Sanchai, Wu Shih-Hsiung, Zou Wei

机构信息

Institute for Biological Sciences, National Research Council of Canada, 100 Sussex Drive, Ottawa, Ontario K1A 0R6, Canada.

出版信息

Org Lett. 2004 Sep 30;6(20):3497-9. doi: 10.1021/ol0486627.

DOI:10.1021/ol0486627

PMID:15387532

Abstract

[reaction: see text] 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.

摘要

[反应：见正文] 在碱性条件下，2'-醛基（丙酮基）2-O-甲磺酸酯（对甲苯磺酸酯）-α-C-糖苷发生分子内S(N)2反应，形成1,2-环丙烷化糖，其在异头碳处与亲核试剂（醇、硫醇和叠氮化物）反应，生成2-C-支链糖苷。相比之下，由2'-酮衍生的1,2-环丙烷仅与硫醇反应，生成2-C-支链硫代糖苷。