M. Matsumoto et al., SYNTHESIS OF RO-2,3,4-TRIDEOXY-BETA-D-ERYTHRO-HEX-3-ENOPYRANOSE AND ITS STEREOSPECIFIC SN2' SUBSTITUTION, Heterocycles, 38(11), 1994, pp. 2377-2381
The chlorination of anhydro-3,4-dideoxy-beta-D-threo-hex-3-enopyranose
(2) with SOCl2 and pyridine gives predominantly -anhydro-2-chloro-bet
a-D-erythro-hex-3-enopyranose (3). The chloride (3) takes place exclus
ively the suprafacial SN2' substitution with a variety of nucleophiles
in DMF. ''Cerny epoxides'' are conveniently synthesized by using the
reaction of 3 with PhCH2ONa.