SYNTHESIS OF RO-2,3,4-TRIDEOXY-BETA-D-ERYTHRO-HEX-3-ENOPYRANOSE AND ITS STEREOSPECIFIC SN2' SUBSTITUTION

Authors
MATSUMOTO M ISHIKAWA H SOYA Y OZAWA T
Citation
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
Citations number
8
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Heterocycles → ACNP
ISSN journal
03855414
Volume
38
Issue
11
Year of publication
1994
Pages
2377 - 2381
Database
ISI
SICI code
0385-5414(1994)38:11<2377:SORAI>2.0.ZU;2-5
Abstract
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.