Synthesis of 5,6-Dideoxy-5-phenylphosphinyl-<scp>l</scp>-galactopyranoses. The P-in-Ring Sugar Analogs of <scp>l</scp>-Fucose

• Tadashi Hanaya

  Department of Chemistry, Faculty of Science, Okayama University

• Hiroshi Yamamoto

  Department of Chemistry, Faculty of Science, Okayama University

• Takeshi Ohmae

  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

抄録

1,2-O-Isopropylidene-3-O-methyl-6-O-tosyl-β-d-arabino-hexofuranos-5-ulose (9a) and its 3-O-benzyl congener (9b) were prepared from 1,2:5,6-di-O-isopropylidene-β-d-altrofuranose in 4 steps. Addition of methyl phenylphosphinate to 9a and 9b in the presence of DBU, followed by reduction with Raney Ni, afforded (5R and 5S)-5,6-dideoxy-1,2-O-isopropylidene-5-[(methoxy)phenylphosphinyl]-3-O-methyl-β-d-arabino-hexofuranose(11a) and 3-O-benzyl congener (11b), respectively. The latter compound (11b) was debenzylated to 3-O-unsubstituted hexofuranose 11d. By reduction with sodium dihydrobis(2-methoxyethoxy)aluminate, followed by acid hydrolysis, these key intermediates 11a, 11b, and 11d provided the title l-fucoses 13 (together with a minor proportion of d-altropyranoses 14) having as phenylphosphinylidene group in place of the ring oxygen. Compounds 13 and 14 were converted into per-O-acetyl derivatives for structural and conformational analysis by spectroscopy.

収録刊行物

• Bulletin of the Chemical Society of Japan

  Bulletin of the Chemical Society of Japan 64 (3), 869-876, 1991-03-01

  Oxford University Press (OUP)

キーワード

• General Chemistry

詳細情報

• CRID: 1360283694080367488
• NII論文ID: 130001978998
• DOI: 10.1246/bcsj.64.869
• ISSN: 13480634
• ISSN: 00092673
• Web Site: https://academic.oup.com/bcsj/article-pdf/64/3/869/56185536/bcsj.64.869.pdf
• データソース種別:
  • Crossref
  • CiNii Articles