Stereocontrolled preparation of cyclic xanthate; a novel synthetic route to 4-thiofuranose and 4′-thionucleoside

…, M Motoyama, Y Nishiyama, S Wakabayashi

Index: Uenishi, Jun'ichi; Motoyama, Mitsuhiro; Nishiyama, Yoshitaka; Wakabayashi, Shoji Journal of the Chemical Society, Chemical Communications, 1991 , # 20 p. 1421 - 1422

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Citation Number: 23

Abstract

Optically active cyclic xanthate was prepared by the reaction of an epoxy alcohol with NaH and CS2, and was found to be a useful intermediate for synthesis of 4-thio-2-deoxyri bose and 4'-thio-2'-deoxyribonucleoside. ... Since optically active epoxy alcohols have been obtained easily by the asymmetric epoxidation of allylic alcoho1,l regio- and stereo-specific ring opening reactions to 2,3-epoxy al- cohol by various types of nucleophiles, intramolecularly2 or ...