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

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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 lb. 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-MHz1H 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
DOIs
Publication statusPublished - Jan 1 1985

ASJC Scopus subject areas

  • Organic Chemistry

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    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. https://doi.org/10.1021/jo00219a018