Synthetic Studies of Potential Antimetabolites. XI. Syntheses of β-D-Pentofuranosyl-5-methylcytosines

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概要

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• 1-(β-D-Arabinofuranosyl)-5-methylcytosine (III) was prepared by amination and subsequent deblocking of 1-(2', 3', 5'-tri-O-benzyl-β-D-arabinofuranosyl)-4-methoxy-5-methyl-1H-pyrimidine-2-one which had been prepared from 2,4-dimethoxy-5-methylpyrimidine and 1-(2', 3', 5'-tri-O-benzyl-α-D-arabinofuranosyl) chloride. 1-(β-D-2'-Deoxy threopentofuranosyl)-5-methylcytosine (II) was prepared from 1-(β-D-3', 5'-O-isopropyl indene-2'-deoxythreopentofuranosyl)-5-methyluracil (VII) by four-step procedure (thiation, S-methylation, amination, and deblocking). As one of possible approaches to II from thymidine (IV), 1-(3', 5'-anhydro-2'-deoxy-β-D-threopentofuranosyl)-thymine (V) was attempted to convert to 1-(3', 5'-anhydro-2'-deoxythreopentofuranosyl)-4-chloro-2 (1H)-pyrimidine-2-one. However, treatment of the latter with DMF-SOCl_2 (Vilsmeier-Haack reagent) afforded 1-(3', 5'-dideoxy-3', 5'-dichloro-2'-deoxythreo pentofruanosyl)-thymine (XIV) in good yield.

• 1968-02-25

著者

• 水野 義久

  School Of Pharmaceutical Sciences Kitasato University

• 水野 義久

  Faculty Of Pharmacy Kanazawa University

• 水野 義久

  北海道大学 薬

• 上田 享

  Faculty of Pharmaceutical Sciences, Hokkaido University

• 池田 一芳

  The Center for Instrumental Analysis of Hokkaido University

• 池田 一芳

  Faculty of Pharmaceutical Sciences, Hokkaido University

• 三浦 一伸

  Faculty Of Pharmaceutical Sciences Hokkaido University

• 上田 享

  Faculty Of Pharmaceutical Sciences Hokkaido University

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