Nucleosides and Nucleotides. VII. Synthesis of 2-Thiocytidine by the Extended Hilbert-Johnson Procedure

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概要

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• Treatment of 4-amino-2-methylthiopyimidine with 2,3,5-tri-O-benzoyl-D-ribosyl chloride afforded the ribosylpyrimidinium chloride (VI), which, on treatment with hydrogen sulfide, gave 2', 3', 5'-tri-O-benzoyl-2-thiocytidine (VII) and 2-thiocytidine (VIII) by further de-benzoylation. Methylation of VIII afforded 2-methylthiopyrimidinium derivative (IX). Treatment of IX (or VI) with methanolic ammonia gave 2,4-diamino-1-(β-D-ribofuranosyl)-pyrimidinium salt. With alkali IX (or VI) gave cytidine. This condensation can be regarded as an extended Hilbert-Johnson procedure for pyrimidine nucleoside synthesis. Relationships between stability of ribosylpyrimidinium salts and structure of their pyrimidines are discussed. The mechanism of the Hilbert-Johnson reaction was established therefrom.

• 公益社団法人日本薬学会の論文
• 1973-07-25

著者

• 上田 亨

  Faculty of Pharmaceutical Science, Hokkaido University

• 大塚(西野) 宏子

  Faculty Of Pharmaceutical Sciences Hokkaido University

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