Tin-mediated regioselective etherification and esterification of unprotected xylitol

摘要

Regioselective alkylation and acylation of xylitol stannylene acetal derivatives with alkyl and acyl halides is reported. The coupling reaction was promoted when necessary by cesium fluoride under mild conditions, affording mono- and di-ethers of xylitol at the primary hydroxyl groups in good overall yields (50-60%). The additional salt was not required in acylation reactions which afforded diesters of xylitol in excellent yields (similar to 96%). (C) 1998 Elsevier Science Ltd. All rights reserved. [References: 16]