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Communication | Regular issue | Vol 38, No. 11, 1994, pp.2377-2381
Published online, 1st January, 1970
DOI: 10.3987/COM-94-6864
Synthesis of 1,6-Anhydro-2-chloro-2,3,4-trideoxy-β-D-erythro-hex-3-enopyranose and Its Stereospecific SN2‘ Substitution

Masakatsu Matsumoto,* Hiromi Ishikawa, Yoshihiro Soya, and Takayuki Ozawa

*Department of Chemistry, Faculty of science, Kanagawa University, 2946 Tsuchiya, Hiratsuka 259-1293, Japan

Abstract

The chlorination of 1,6--anhydro3,4-dideoxy-β-D-threo-hex-3-enopyranose (2) with SOCl2 and pyridine gives predominantly 1,6-anhydro-2-chloro-β-D-erythro-hex-3-enopyranose (3). The chloride (3) takes place exclusively the suprafacial SN2‘ substitution with a variety of nucleophiles in DMF. "Cerny epoxides" are conveniently synthesized by using the reaction of 3 with PhCH2ONa.