Acetonation of D-xylose diethyl dithioacetal

Abstract

The acetonation of d-xylose diethyl dithioacetal yields the 2,3;4,5-di-O-isopropylidene derivative. Partial acetonation yields the 4,5-, 3,4-, 2,3-, and 2,4-O-isopropylidene derivatives, the structures of which have been proved. The acetonation of the 2,4-O-isopropylidene derivative gives the 2,4;3,5-di-O-isopropylidene derivative. New preparations of 2,3- and 2,5-di-O-methyl-d-xylose, and the preparation of crystalline methyl 2,3-di-O-methyl-α-d-xylofuranoside, are described.