Synthesis of 5-Deoxy-5-phenylphosphino- and 5-Phenylphosphinyl-<scp>d</scp>-glucopyranoses

• Tadashi Hanaya

  Department of Chemistry, Faculty of Science, Okayama University

• Akihito Akamatsu

  Department of Chemistry, Faculty of Science, Okayama University

• Heizan Kawamoto

  Department of Chemistry, Faculty of Science, Okayama University

• Margaret-Ann Armour

  Department of Chemistry, University of Alberta

• Alan M Hogg

  Department of Chemistry, University of Alberta

• Hiroshi Yamamoto

  Department of Chemistry, Faculty of Science, Okayama University

抄録

(5R and 5S)-3-O-Acetyl-5-deoxy-1,2-O-isopropylidene-5-[(methoxy)phenylphosphinyl]-6-O-(tetrahydro-2-pyranyl)-α-d-xylo-hexofuranoses (7) were prepared from 3-O-acetyl-5,6-dideoxy-6-nitro-α-d-xylo-hex-5-enofuranose in 4 steps. Reduction of 7 with sodium dihydridobis(2-methoxyethoxy)aluminate followed by acid hydrolysis provided the title compounds, among which the 5-deoxy-5-phenylphosphino-d-glucoses are the first example of hexopyranose analogs having a phosphinidene group in place of hemiacetal ring-oxygen. These compounds were converted into 1,2,3,4,6-penta-O-acetates, whose structures were established by spectroscopy.

収録刊行物

• Bulletin of the Chemical Society of Japan

  Bulletin of the Chemical Society of Japan 64 (8), 2398-2401, 1991-08-01

  Oxford University Press (OUP)

キーワード

• General Chemistry

詳細情報

• CRID: 1360565169056978944
• NII論文ID: 130001978803
• DOI: 10.1246/bcsj.64.2398
• ISSN: 13480634
• ISSN: 00092673
• Web Site: https://academic.oup.com/bcsj/article-pdf/64/8/2398/56186130/bcsj.64.2398.pdf
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