Studies on Antitumor Agents. IX. : Synthesis of 3'-O-Benzyl-2'-deoxy-5-trifluoromethyluridine

• 山下 純一

  Kodama Institute, Taiho Pharmaceutical Co., Ltd.,

• 松本 宏

  Tokushima Institute, Taiho Pharmaceutical Co., Ltd.,

• 小林 和弘

  Kodama Institute, Taiho Pharmaceutical Co., Ltd.,

• 野口 和春

  Kodama Institute, Taiho Pharmaceutical Co., Ltd.,

• 安本 三治

  Kodama Institute, Taiho Pharmaceutical Co., Ltd.,

• 上田 亨

  Faculty of Pharmaceutical Science, Hokkaido University

抄録

A practical synthesis of 3'-O-benzyl-2'-deoxy-5-trifluoromethyluridine (1), a candidate antitumor agent for clinical testing, was developed from 2'-deoxy-5-iodouridine (3). Benzylation of 2'-deoxy-5-iodo-5'-O-trityluridine (14) with benzyl bromide and sodium hydride in tetrahydrofuran gave the 3'-O-derivative (16). Benzoylation of 16 afforded the N^3-benzoyl derivative (17). Coupling of 17 with trifluoromethylcopper, prepared from bromotrifluoromethane and copper powder in the presence of 4-dimethylaminopyridine, gave the 5-trifluoromethyl derivative (19) minimally contaminated with the 5-pentafluoroethyl compound. Deprotection of 19 furnished 1.

収録刊行物

• Chemical & pharmaceutical bulletin

  Chemical & pharmaceutical bulletin 37 (9), 2287-2292, 1989-09-25

  公益社団法人日本薬学会

キーワード

• 3'-O-benzyl-2'-deoxy-5-trifluoromethyluridine
• antitumor activity
• 2'-deoxy-5-iodouridine
• O-benzylation
• trifluoromethylation
• bromotrifluoromethane
• trifluoromethylcopper

詳細情報

• CRID: 1572824502321870080
• NII論文ID: 110003627983
• NII書誌ID: AA00602100
• ISSN: 00092363
• 本文言語コード: en
• データソース種別:
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