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

Tadashi Hanaya, Kunihiro Hirose, Hiroshi Yamamoto

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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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Rubiaceae
Sugars
Conformations
Spectrum Analysis
Spectroscopy
Derivatives
propylene

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  • Organic Chemistry

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

Synthesis of 5-deoxy-5-hydroxyphosphinyl-d-mannopyranoses. / Hanaya, Tadashi; Hirose, Kunihiro; Yamamoto, Hiroshi.

In: Heterocycles, Vol. 36, No. 11, 01.11.1993, p. 2557-2564.

Research output: Contribution to journalArticle

Hanaya, T, Hirose, K & Yamamoto, H 1993, 'Synthesis of 5-deoxy-5-hydroxyphosphinyl-d-mannopyranoses', Heterocycles, vol. 36, no. 11, pp. 2557-2564.
Hanaya T, Hirose K, Yamamoto H. Synthesis of 5-deoxy-5-hydroxyphosphinyl-d-mannopyranoses. Heterocycles. 1993 Nov 1;36(11):2557-2564.
Hanaya, Tadashi ; Hirose, Kunihiro ; Yamamoto, Hiroshi. / Synthesis of 5-deoxy-5-hydroxyphosphinyl-d-mannopyranoses. In: Heterocycles. 1993 ; Vol. 36, No. 11. pp. 2557-2564.
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