2-C-Branched Glycosides from 2‘-Carbonylalkyl 2-O-Ms(Ts)-C-Glycosides. A Tandem SN2−SN2 Reaction via 1,2-Cyclopropanated Sugars

Autor: Shao, H., Ekthawatchai, S., Wu, S.-H., Zou, W.
Zdroj: Organic Letters; September 2004, Vol. 6 Issue: 20 p3497-3499, 3p
Abstrakt: Under basic conditions, 2‘-aldehydo (acetonyl) 2-O-Ms(Ts)-α-C-glycosides undergo an intramolecular SN2 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.
Databáze: Supplemental Index