2-C-branched glycosides from 2'-carbonylalkyl 2-O-Ms(Ts)-C-glycosides. A tandem SN2-SN2 reaction via 1,2-cyclopropanated sugars.
[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.
Shao
Huawu
H
Institute for Biological Sciences, National Research Council of Canada, 100 Sussex Drive, Ottawa, Ontario K1A 0R6, Canada.
Ekthawatchai
Sanchai
S
Wu
Shih-Hsiung
SH
Zou
Wei
W
D002384:Catalysis; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry*; D007202:Indicators and Reagents; D015394:Molecular Structure; D013237:Stereoisomerism; D013438:Sulfhydryl Compounds / Q000737:chemistry
D006027:Glycosides; D007202:Indicators and Reagents; D013438:Sulfhydryl Compounds