Synthesis of 6,3'-Methanocytidine, 6,3'-Methanouridine, and Their 2'-Deoxyribonucleosides (Nucleosides and Nucleotides. LXXVII)

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概要

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• Condensation of 5-O-tert-butyldimethylsilyl-1,2-O-isopropylidene-α-D-erythro-3-pentulo-furanose (4) with 2,4-dimethoxypyrimidin-6-ylmethyllithium (5) afforded a 3-pyrimidinylmethyl-ribose derivative (6). The protecting groups of 6 were changed to give the 5-O-benzoyl-1,2-di-O-acetyl derivative (8). The intramolecular glycosylation of 8 by treatment with stannic chloride furnished the 6,3'-methanol-O^4-methyluridine derivative (9), which was further converted to 6,3'-methanouridine (10) and 6,3'-methanocytidine (11). The 2'-deoxygenation of 9 by way of the 2'-imidazolylthiocarbonyl dericative gave, after appropriate derivatization, 2'-deoxy-6,3'-methanocytidine (16) and -uridine (17).

• 社団法人日本薬学会の論文
• 1988-01-25

著者

• 上田 亨

  Faculty of Pharmaceutical Science, Hokkaido University

• 松田 彰

  Faculty Of Pharmaceutical Sciences Hokkaido University

• 上田 亨

  Faculty Of Pharmaceutical Sciences Hokkaido University

• 吉村 祐一

  Faculty Of Pharmaceutical Sciences Hokkaido University

• 佐野 友春

  Faculty of Pharmaceutical Sciences, Hokkaido University

• 佐野 友春

  Faculty Of Pharmaceutical Sciences Hokkaido University

• 上田 亨

  北海道大学薬学部

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