Straightforward Route for Anchoring a Glucosyl Moiety onto Nucleophilic Species: Reaction of Amines and Alcohols with Carboxymethyl 3,4,6-Tri-<i>O</i>-acetyl-α-<scp>d</scp>-glucopyranoside 2-<i>O</i>-Lactone

Abstract

The base-catalyzed reaction of carboxymethyl 3,4,6-tri-O-acetyl-alpha-D-glucopyranoside 2-O-lactone (prepared from isomaltulose) with amino acids and fatty amines under basic catalysis gave a series of new pseudoglucopeptides, nonionic amphiphiles, and polymerizable derivatives. The same reaction applied to alcohols provided the corresponding 2-(alpha-D-glucopyranosyloxy)acetyl esters with either basic or acidic catalysts.