Studies on the Synthesis of Pyrimidine Deoxynucleosides. I. Synthesis of 2', 3'-Dideoxyuridine and 1-(3-Ethylthio-3-deoxy-β-D-xylofuranosyl) uracil

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概要

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• Treatment of 2,2'-anhydro-1-(3,5-di-O-acetyl-β-D-arabinofuranosyl) uracil (II) with sodium ethanethiol afforded 1-(3-ethylthio-3-deoxy-β-D-xylofuranosyl) uracil (IV) in 90% yield. Hydrogenation of 2,2'-anhydro-1-(5-O-benzoyl-3-O-mesyl-β-D-arabinofuranosyl)-uracil (III) with Raney nickel resulted in formation of the 5,6-dihydro derivative (VI). 5'-O-Benzoyl-2'-bromo-2'-deoxy-3'-O-mesyluridine (VII) was hydrogenated in the presence of Pd・BaSO_4 or Raney nickel to yield 5'-O-benzoyl-2', 3'-dideoxyruidine (VIII). VIII was treated with alkali to give 2', 3'-dideoxyuridine (IX) in 50% overall yield from uridine. The mechanism of the reductive elimination of the cis-bromohydrin mesylate (VII) was presented. The treatment of VII with sodium methoxide in methanol gave 1-(2-bromo-2,3-dideoxy-2-ene-β-D-glyceropentofuranosyl) uracil (XII) which was converted to IX by the catalytic hydrogenation. Bromination of IX afforded 5-bromo-2', 3'-dideoxyuridine (XIV).

• 社団法人日本薬学会の論文
• 1970-03-25

著者

• 吉岡 義夫

  Chemical Research Laboratories, Central Research Division, Takeda Chemical Industries, Ltd.

• 古川 純康

  Chemical Research Laboratories, Central Research Division, Takeda Chemical Industries, Ltd.

• 本庄 美喜男

  Chemical Research Laboratories, Central Research Division, Takeda Chemical Industries, Ltd.

• 吉岡 義夫

  Central Research Division Takeda Chemical Ind. Ltd.

• 今井 欣一

  Animal Health Products Division Takeda Chemical Industries Ltd.

• 今井 欣一

  Chemical Research Laboratories, Research and Development Division, Takeda Chemical Industries, Ltd.

• 本庄 美喜男

  Faculty Of Pharmaceutical Sciences Tokushima Bunri University

• 古川 純康

  Chemistry Laboratories Central Research Division Takeda Chemical Industries Ltd.

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