Formation and characterization of 5-C-[(R)-(1-acetoxy-ethenyl)phosphinyl]-1,2,4-tri-O-acetyl-5-deoxy-3-O-methyl-β-d-xylopyranose

Hiroshi Yamamoto, Tadashi Hanaya, Saburo Inokawa, Margaret Ann Armour

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

Treatment of 5-deoxy-3-O-methyl-5-C-phosphinyl-d-xylopyranose with acetic anhydride in pyridine gave, along with other products, a peracetylated derivative, to which the title structure was assigned on the basis of 400-MHz, 1H-n.m.r. and high-resolution mass spectra. The previous, 5-C-[(S)-(1-acetoxyethenyl)phosphino] structure, presented for the by-product during the preparation of tri-O-acetyl-5-deoxy-5-C-(methoxyphosphinyl)-3-O-methyl-d- xylopyranoses, is now replaced by the new formulation. Possible structures of other products of the acetylation are discussed. Analysis of the mass spectrum of a sugar analog having a 5-deoxy-5-C-(phosphinyl)-d-xylopyranose ring-system is made.

Original languageEnglish
Pages (from-to)195-200
Number of pages6
JournalCarbohydrate Research
Volume124
Issue number2
DOIs
Publication statusPublished - Dec 23 1983

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Acetylation
Sugars
Byproducts
Mass Spectrometry
Derivatives
xylopyranose
pyridine
acetic anhydride

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry

Cite this

Formation and characterization of 5-C-[(R)-(1-acetoxy-ethenyl)phosphinyl]-1,2,4-tri-O-acetyl-5-deoxy-3-O-methyl-β-d-xylopyranose. / Yamamoto, Hiroshi; Hanaya, Tadashi; Inokawa, Saburo; Armour, Margaret Ann.

In: Carbohydrate Research, Vol. 124, No. 2, 23.12.1983, p. 195-200.

Research output: Contribution to journalArticle

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abstract = "Treatment of 5-deoxy-3-O-methyl-5-C-phosphinyl-d-xylopyranose with acetic anhydride in pyridine gave, along with other products, a peracetylated derivative, to which the title structure was assigned on the basis of 400-MHz, 1H-n.m.r. and high-resolution mass spectra. The previous, 5-C-[(S)-(1-acetoxyethenyl)phosphino] structure, presented for the by-product during the preparation of tri-O-acetyl-5-deoxy-5-C-(methoxyphosphinyl)-3-O-methyl-d- xylopyranoses, is now replaced by the new formulation. Possible structures of other products of the acetylation are discussed. Analysis of the mass spectrum of a sugar analog having a 5-deoxy-5-C-(phosphinyl)-d-xylopyranose ring-system is made.",
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AB - Treatment of 5-deoxy-3-O-methyl-5-C-phosphinyl-d-xylopyranose with acetic anhydride in pyridine gave, along with other products, a peracetylated derivative, to which the title structure was assigned on the basis of 400-MHz, 1H-n.m.r. and high-resolution mass spectra. The previous, 5-C-[(S)-(1-acetoxyethenyl)phosphino] structure, presented for the by-product during the preparation of tri-O-acetyl-5-deoxy-5-C-(methoxyphosphinyl)-3-O-methyl-d- xylopyranoses, is now replaced by the new formulation. Possible structures of other products of the acetylation are discussed. Analysis of the mass spectrum of a sugar analog having a 5-deoxy-5-C-(phosphinyl)-d-xylopyranose ring-system is made.

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