The Journal of Organic Chemistry

Stereocontrolled routes to functionalized C-glycopyranosides

RD Dawe, B Fraser-Reid

Index: Dawe, Robert David; Fraser-Reid, Bert Journal of Organic Chemistry, 1984 , vol. 49, # 3 p. 522 - 528

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Citation Number: 84

Abstract

4, 6-O-Ethylidene-~-glucopyranose (1) reacts with an acid-washed, stabilized Wittig reagent to give the trans-oct-2-enoate 2 in excellent yield. Cyclization is effected by treatment with dilute base, and after 1 h, a 1: l mixture of anomers exists which is the optimum concentration of the CY-D form. Continuing base treatment for 5 h leads to the (3-D anomer exclusively. aDC-Glycopyranosides can be obtained as predominant products by Lewis ...