Nucleosides and nucleotides. XIV. Synthesis of 6-alkylthiouridines and uridine-6-sulfonic acid.

• 井上 英夫

• 富田 節子

• 上田 亨

抄録

Treatment of 5'-O-acetyl-2', 3'-O-isopropylidene-5-bromouridine with benzyl mercaptan yielded both 5-benzylthio and 6-benzylthio derivatives, (IIa) and (IIIa). Deprotection of those derivatives gave 5-benzylthiouridine (IIc) and 6-benzylthiouridine (IIIc). Treatment of IIIa with methoxide followed by H₂S afforded 2', 3'-O-isopropylidene-6-thiouridine (IV). Methylation of IV gave 6-methylthiouridine (VI) after deblocking. Oxidation of IV with hydrogen peroxide afforded uridine-6-sulfonic acid (VII), an orotidine analog. Nuclear magnetic resonance and circular dichroism data were given and conformations of these nucleosides were discussed.

収録刊行物

• ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ

  ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ 23 (11), 2614-2619, 1975

  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: 1390282679149644672
• NII論文ID: 110003621748
• NII書誌ID: AA00602100
• DOI: 10.1248/cpb.23.2614
• ISSN: 13475223
• ISSN: 00092363
• Web Site: http://www.jstage.jst.go.jp/article/cpb1958/23/11/23_11_2614/_pdf
• Web Site: https://search.jamas.or.jp/link/ui/1976106815
• 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