A convenient synthesis of 1,2,4-Tri-O-acetyl-5-deoxy-5-[(R)- and (S)-ethylphosphino and phenylphosphino]-3-O-methyl-α,β-D- xylopranoses and their phosphinothioyl derivatives section

Tadashi Hanaya, N. Shigetoh, H. Yamamoto, M. A. Armour, A. M. Hogg

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Abstract

1,2,4-Tri-O-acetyl-5-deoxy-5-[(R)- and (S)-ethylophosphinyl]-3-O-methyl-α,β-D-xylopyranoses (8a - d) were prepared from 5-deoxy-5-[(R)- and (S)-(ethoxy)ethylphosphinyl]-1,2-O-isopropylidene-3-O-methyl-α-D- xylofuranoses in two steps. Reduction of 8a - d and their 5-(phenylphosphinyl) congeners with trichlorosi-lane-triethylamine in benzene smoothly afforded the corresponding title 5-deoxy-5-phosphino-D-xylopyranoses (9a - d and 14a - d) without causing inversion of the ring-phosphorus atom. Treatment of 9a - d and 14a - d with sulfur in benzene efficiently provided the corresponding (phosphinothioyl)-in-ring D-xylopyranoses. Structural and conformational assignments of these newly obtained compounds were made on the basis of mass and NMR (1H and 31P) spectral data.

Original languageEnglish
Pages (from-to)421-427
Number of pages7
JournalBulletin of the Chemical Society of Japan
Volume63
Issue number2
DOIs
Publication statusPublished - 1990

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Benzene
Derivatives
Sulfur
Phosphorus
Nuclear magnetic resonance
Atoms
triethylamine
propylene

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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title = "A convenient synthesis of 1,2,4-Tri-O-acetyl-5-deoxy-5-[(R)- and (S)-ethylphosphino and phenylphosphino]-3-O-methyl-α,β-D- xylopranoses and their phosphinothioyl derivatives section",
abstract = "1,2,4-Tri-O-acetyl-5-deoxy-5-[(R)- and (S)-ethylophosphinyl]-3-O-methyl-α,β-D-xylopyranoses (8a - d) were prepared from 5-deoxy-5-[(R)- and (S)-(ethoxy)ethylphosphinyl]-1,2-O-isopropylidene-3-O-methyl-α-D- xylofuranoses in two steps. Reduction of 8a - d and their 5-(phenylphosphinyl) congeners with trichlorosi-lane-triethylamine in benzene smoothly afforded the corresponding title 5-deoxy-5-phosphino-D-xylopyranoses (9a - d and 14a - d) without causing inversion of the ring-phosphorus atom. Treatment of 9a - d and 14a - d with sulfur in benzene efficiently provided the corresponding (phosphinothioyl)-in-ring D-xylopyranoses. Structural and conformational assignments of these newly obtained compounds were made on the basis of mass and NMR (1H and 31P) spectral data.",
author = "Tadashi Hanaya and N. Shigetoh and H. Yamamoto and Armour, {M. A.} and Hogg, {A. M.}",
year = "1990",
doi = "10.1246/bcsj.63.421",
language = "English",
volume = "63",
pages = "421--427",
journal = "Bulletin of the Chemical Society of Japan",
issn = "0009-2673",
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TY - JOUR

T1 - A convenient synthesis of 1,2,4-Tri-O-acetyl-5-deoxy-5-[(R)- and (S)-ethylphosphino and phenylphosphino]-3-O-methyl-α,β-D- xylopranoses and their phosphinothioyl derivatives section

AU - Hanaya, Tadashi

AU - Shigetoh, N.

AU - Yamamoto, H.

AU - Armour, M. A.

AU - Hogg, A. M.

PY - 1990

Y1 - 1990

N2 - 1,2,4-Tri-O-acetyl-5-deoxy-5-[(R)- and (S)-ethylophosphinyl]-3-O-methyl-α,β-D-xylopyranoses (8a - d) were prepared from 5-deoxy-5-[(R)- and (S)-(ethoxy)ethylphosphinyl]-1,2-O-isopropylidene-3-O-methyl-α-D- xylofuranoses in two steps. Reduction of 8a - d and their 5-(phenylphosphinyl) congeners with trichlorosi-lane-triethylamine in benzene smoothly afforded the corresponding title 5-deoxy-5-phosphino-D-xylopyranoses (9a - d and 14a - d) without causing inversion of the ring-phosphorus atom. Treatment of 9a - d and 14a - d with sulfur in benzene efficiently provided the corresponding (phosphinothioyl)-in-ring D-xylopyranoses. Structural and conformational assignments of these newly obtained compounds were made on the basis of mass and NMR (1H and 31P) spectral data.

AB - 1,2,4-Tri-O-acetyl-5-deoxy-5-[(R)- and (S)-ethylophosphinyl]-3-O-methyl-α,β-D-xylopyranoses (8a - d) were prepared from 5-deoxy-5-[(R)- and (S)-(ethoxy)ethylphosphinyl]-1,2-O-isopropylidene-3-O-methyl-α-D- xylofuranoses in two steps. Reduction of 8a - d and their 5-(phenylphosphinyl) congeners with trichlorosi-lane-triethylamine in benzene smoothly afforded the corresponding title 5-deoxy-5-phosphino-D-xylopyranoses (9a - d and 14a - d) without causing inversion of the ring-phosphorus atom. Treatment of 9a - d and 14a - d with sulfur in benzene efficiently provided the corresponding (phosphinothioyl)-in-ring D-xylopyranoses. Structural and conformational assignments of these newly obtained compounds were made on the basis of mass and NMR (1H and 31P) spectral data.

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