Stereocontrolled general synthesis of pyrimidine C-nucleosides having branched-chain sugar moieties.

…, M Watanabe, H Kobayashi, R Noyori

Index: Sato; Watanabe; Kobayashi; Noyori Bulletin of the Chemical Society of Japan, 1983 , vol. 56, # 9 p. 2680 - 2699

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Citation Number: 12

Abstract

A variety of pyrimidine C-nucleosides bearing branched-chain sugars can be synthesized starting from adequately substituted (1R*, 6S*, 7S*, 8R*)-7, 8-isopropylidenedioxy-3, 9- dioxabicyclo [4.2. 1] nonan-4-ones. The general procedure consists of condensation with t- butoxybis (dimethylamino) methane, giving the corresponding α-dimethylaminomethylene lactones, base-catalyzed heterocycle formation with urea, thiourea, or guanidine, and acid ...