Synthesis of 5-deoxy-5-hydroxyphosphinyl-d-mannopyranoses

Tadashi Hanaya, Kunihiro Hirose, Hiroshi Yamamoto

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8 Citations (Scopus)

Abstract

The title sugar analogues (13) were synthesized by starting with known methyl (E)-5,6-dideoxy-2,3-O-isopropylidene-6-nitro-α-d-lyxo-hex-5-enofuranoside (5a) in six steps through the key intermediate, methyl 5-deoxy-5-dimethoxy-phosphinyl-2,3-O-isopropylidene-α-d-mannofuranoside 8a). The products (13) were converted into the corresponding penta-O-acetyl-5-methoxyphosphinyl derivatives (14), whose structures and conformations (mostly 4C1) were established by spectroscopy.

Original languageEnglish
Pages (from-to)2557-2564
Number of pages8
JournalHeterocycles
Volume36
Issue number11
Publication statusPublished - Nov 1 1993

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ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

Cite this

Hanaya, T., Hirose, K., & Yamamoto, H. (1993). Synthesis of 5-deoxy-5-hydroxyphosphinyl-d-mannopyranoses. Heterocycles, 36(11), 2557-2564.