Studies on organic fluorine compounds. XXXIX.^<1)> Studies on steroids. LXXIX.^<2)> Synthesis of 1,25-dihydroxy-26,26,26,27,27,27-Hexafluorovitamin D_3

• KOBAYASHI Y

  Tokyo College of Pharmacy

• TAGUCHI TAKEO

  Tokyo College of Pharmacy

• MITSUHASHI SATOSHI

  Tokyo College of Pharmacy

• EGUCHI TADASHI

  Department of Chemistry, Tokyo Institute of Technology

• OHSHIMA ETSUO

  Department of Chemistry, Tokyo Institute of Technology

• IKEKAWA NOBUO

  Department of Chemistry, Tokyo Institute of Technology

Abstract

1α, 25-Dihydroxy-26,26,26,27,27,27-hexafluorocholesterol was synthesized by two procedures. Cholenic acid was converted to the 1α-hydroxy-24-sulfone derivative and hexafluoroacetone was reacted with the lithiated 24-sulfone. Subsequent removal of the sulfonyl group afforded the hexafluoro-1α, 25-dihydroxy compound. An alternative process consists of construction of the hexafluoro-25-hydroxy part on the side chain followed by the introduction of a hydroxy group at the 1α-position. The hexafluoro derivative was converted to the vitamin D form, 1α, 25-dihydroxyhexafluorovitamin D_3,via the corresponding 5,7-diene.

Journal

• Chem. Pharm. Bull.

  Chem. Pharm. Bull. 30 4297-4303, 1982

  The Pharmaceutical Society of Japan

Keywords

• vitamin D_3
• fluoride substitution
• 26-hydroxylation
• hexafluoroacetone
• 26, 26, 26, 27, 27, 27-hexafluoro-1α, 25-dihydroxyvitamin D_3

Details

• CRID: 1570572702395693312
• NII Article ID: 110003634240
• NII Book ID: AA00602100
• ISSN: 00092363
• Web Site: https://search.jamas.or.jp/link/ui/1984171784
• Text Lang: en
• Data Source:
  • CiNii Articles