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

• 古川 純康

• 吉岡 義夫

• 今井 欣一

• 本庄 美喜男

抄録

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·BaSO₄ 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).

収録刊行物

• ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ

  ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ 18 (3), 554-560, 1970

  公益社団法人 日本薬学会

キーワード

• Drug Discovery
• General Chemistry
• General Medicine

詳細情報

• CRID: 1390282679148711296
• NII論文ID: 110003632330
• NII書誌ID: AA00602100
• DOI: 10.1248/cpb.18.554
• ISSN: 13475223
• ISSN: 00092363
• Web Site: http://www.jstage.jst.go.jp/article/cpb1958/18/3/18_3_554/_pdf
• Web Site: https://search.jamas.or.jp/link/ui/1971047180
• 本文言語コード: en
• データソース種別:
  • JaLC
  • Crossref
  • CiNii Articles
• 抄録ライセンスフラグ: 使用不可