Synthesis and structural analysis of 5-deoxy-5-C-(hydroxyphosphinyl)-D-xylo- and -glucopyranoses

Hiroshi Yamamoto, Tadashi Hanaya, Heizan Kawamoto, Saburo Inokawa, Mitsuji Yamashita, Margaret Ann Armour, Thomas T. Nakashima

Research output: Contribution to journalArticle

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Abstract

Treatment of 3-O-acetyl-5-deoxy-5-C-(diethoxyphosphinyl)-1,2-O-isopropylidene-α-D- xylofuranose (1c) with sodium dihydrobis(methoxyethoxy)aluminate, followed by the action of mineral acid and hydrogen peroxide, gave 5-deoxy-5-C-(hydroxyphosphinyl)-D-xylopyranose (4a). The 3-O-benzyl derivative 4c was similarly obtained from the corresponding 3-O-benzyl-α-D-xylofuranose 1b. Diazotization of 3-O-acetyl-6-amino-5,6-dideoxy-5-C-(dimethoxyphosphinyl)-1,2-O-isopropylidene- α-D-glucofuranose (12), followed by hydrolysis and then treatment with chlorotriphenylmethane in pyridine, afforded the corresponding 5-deoxy-6-O-triphenylmethyl derivative 17. Similar ring enlargement of 17 exclusively yielded 5-deoxy-5-C-(hydroxyphosphinyl)-D-glucopyranose. The structures of these phosphorus sugar analogues were established on the basis of mass and 400-MHz 1H NMR spectra of the per-O-acetyl-5-deoxy-5-C-(methoxyphosphinyl) derivatives 6-9 and 21-25.

Original languageEnglish
Pages (from-to)3516-3521
Number of pages6
JournalJournal of Organic Chemistry
Volume50
Issue number19
Publication statusPublished - 1985

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Structural analysis
Derivatives
Sugars
Phosphorus
Hydrogen Peroxide
Minerals
Hydrolysis
Sodium
Nuclear magnetic resonance
Acids
1,2-O-isopropylidene-D-glucofuranose
xylopyranose
pyridine
propylene

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Yamamoto, H., Hanaya, T., Kawamoto, H., Inokawa, S., Yamashita, M., Armour, M. A., & Nakashima, T. T. (1985). Synthesis and structural analysis of 5-deoxy-5-C-(hydroxyphosphinyl)-D-xylo- and -glucopyranoses. Journal of Organic Chemistry, 50(19), 3516-3521.

Synthesis and structural analysis of 5-deoxy-5-C-(hydroxyphosphinyl)-D-xylo- and -glucopyranoses. / Yamamoto, Hiroshi; Hanaya, Tadashi; Kawamoto, Heizan; Inokawa, Saburo; Yamashita, Mitsuji; Armour, Margaret Ann; Nakashima, Thomas T.

In: Journal of Organic Chemistry, Vol. 50, No. 19, 1985, p. 3516-3521.

Research output: Contribution to journalArticle

Yamamoto, H, Hanaya, T, Kawamoto, H, Inokawa, S, Yamashita, M, Armour, MA & Nakashima, TT 1985, 'Synthesis and structural analysis of 5-deoxy-5-C-(hydroxyphosphinyl)-D-xylo- and -glucopyranoses', Journal of Organic Chemistry, vol. 50, no. 19, pp. 3516-3521.
Yamamoto H, Hanaya T, Kawamoto H, Inokawa S, Yamashita M, Armour MA et al. Synthesis and structural analysis of 5-deoxy-5-C-(hydroxyphosphinyl)-D-xylo- and -glucopyranoses. Journal of Organic Chemistry. 1985;50(19):3516-3521.
Yamamoto, Hiroshi ; Hanaya, Tadashi ; Kawamoto, Heizan ; Inokawa, Saburo ; Yamashita, Mitsuji ; Armour, Margaret Ann ; Nakashima, Thomas T. / Synthesis and structural analysis of 5-deoxy-5-C-(hydroxyphosphinyl)-D-xylo- and -glucopyranoses. In: Journal of Organic Chemistry. 1985 ; Vol. 50, No. 19. pp. 3516-3521.
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