Selective esterification of sucrose using pivaloyl chloride

Abstract

Crystalline 1′,3,3′,4′,6,6′-hexa-O-pivaloylsucrose (2), a 2,4-diol, has been isolated directly in 45% yield from the reaction of sucrose with pivaloyl chloride in pyridine; by variation of the reaction conditions, a variety of penta-[(1) and (4)], hexa-[(5) and (7)], and hepta-pivalates [(3), (6), and (8)] have been isolated after column chromatography.