Unexpected stereocontrolled access to 1α,1'β-disaccharides from methyl 1,2-ortho esters

J Org Chem. 2012 Jan 6;77(1):795-800. doi: 10.1021/jo202335n. Epub 2011 Dec 15.

Abstract

Mannopyranose-derived methyl 1,2-orthoacetates (R = Me) and 1,2-orthobenzoates (R = Ph) undergo stereoselective formation of 1α,1'β-disaccharides, upon treatment with BF(3)·Et(2)O in CH(2)Cl(2), rather than the expected acid-catalyzed reaction leading to methyl glycosides by way of a rearrangement-glycosylation process of the liberated methanol.