CHIMIE DES SUCRES SANS GROUPEMENTS PROTECTEURS: ESTERIFICATION REGIOSELECTIVE DE L'HYDROXYLE ANOMERE DU LACTOSE LIBRE

Article abstract of DOI:10.1016/S0040-4039(00)81507-5

Treatment of α-lactose with acyl chlorides failed to give any pure products.However, the anomeric hydroxyl of lactose was esterified selectively and in high yields, by treating the free sugar with reactive acylating agents such as N-acyl thiazolidine-thiones or esters of p-nitrophenol, mercapto-benzothiazole and 8-hydroxy quinoline, making thus unnecessary the preliminary protection of the other hydroxyls of the lactose molecule.This appears to be one of the very few selective modifications of sugars known, which do not involve the classical protection-deprotection methodology.