Lipase-Catalyzed 1,6-Acylation of D-Mannitol

Abstract

The selective synthesis of 1,6-diacyl d-mannitols from 2,2,2-trifluoroethyl esters using transesterification, catalyzed by lipases, has been investigated, and the results have been compared with those obtained from a typical acid chloride procedure and a phenylboronic acid-assisted approach. Three commercially available lipases and five 2,2,2-trifluoroethyl esters were examined. In most cases, the yields obtained from the lipase reactions were superior to those produced from either of the other two methods.