A New Activating Principle in Glycoside Synthesis Based on Electrophile-Induced Lactonization of Glucosyl 4-Pentenoates

Publisher Website
Google Scholar
Abstract
After activation with soft electrophiles, e.g. iodonium compounds or 1,3-dithian-2-ylium tetrafluoroborate, O-benzyl-, O-acyl- and N-acyl-protected glycosyl 4-pentenoates 2, prepared by the condensation of the corresponding glucopyranoses 1 with 4-pentenoic acid using diisopropylcarbodiimide, react with alcohols to give the corresponding glycosides 3. This glycosylation proceeds as an electrophile-induced lactonization during which the γ-lactones 4 are formed as the leaving groups at the anomeric center.

This publication has 0 references indexed in Scilit: