Synthesis of 1,2,4-tri-O-acetyl-5-deoxy-5-C-[(R and S)-methoxy-phosphinyl]-3-O-methyl-α- and -β-d-xylopyranose, and their structural analysis by 400-MHz, proton nuclear magnetic resonance spectroscopy

Hiroshi Yamamoto, Tadashi Hanaya, Saburo Inokawa, Kuniaki Seo, Margaret Ann Armour, Tom T. Nakashima

Research output: Contribution to journalArticle

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Abstract

5-Deoxy-5-iodo-1,2-O-isopropylidene-3-O-methyl-α-d-xylofuranose, prepared quantitatively from its 5-O p-tolylsulfonyl precursor, readily gave the 5-C-(diethoxy-phosphinyl) derivative. Treatment of this compound with sodium dihydrobis(2-methoxyethoxy)aluminate, followed by hydrogen peroxide, mineral acid, and hydrogen peroxide, yielded 5-deoxy-5-C-(hydroxyphosphinyl)-3-O-methyl-α,β-d-xylopyranoses in 65% overall yield. The structures of these sugar analogs were effectively established on the basis of the mass and 400-MHz, 1H-n.m.r. spectra of the four title compounds, derived by treatment with diazomethane and then acetic anhydride in pyridine. 5-C-[(S)-(1-Acetoxyethenyl)phosphino]-1,2,4-tri-O-acetyl-5-deoxy-3-O-methyl-β-d-xylopyranose was also isolated and characterized.

Original languageEnglish
Pages (from-to)83-93
Number of pages11
JournalCarbohydrate Research
Volume114
Issue number1
DOIs
Publication statusPublished - Mar 16 1983

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Structural analysis
Hydrogen Peroxide
Nuclear magnetic resonance spectroscopy
Magnetic Resonance Spectroscopy
Sodium Compounds
Nuclear magnetic resonance
Diazomethane
Sugars
Minerals
Sodium
Derivatives
Acids
xylopyranose
Proton Magnetic Resonance Spectroscopy
pyridine
propylene
dihydrobis(2-methoxyethoxy)aluminate
acetic anhydride

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry

Cite this

Synthesis of 1,2,4-tri-O-acetyl-5-deoxy-5-C-[(R and S)-methoxy-phosphinyl]-3-O-methyl-α- and -β-d-xylopyranose, and their structural analysis by 400-MHz, proton nuclear magnetic resonance spectroscopy. / Yamamoto, Hiroshi; Hanaya, Tadashi; Inokawa, Saburo; Seo, Kuniaki; Armour, Margaret Ann; Nakashima, Tom T.

In: Carbohydrate Research, Vol. 114, No. 1, 16.03.1983, p. 83-93.

Research output: Contribution to journalArticle

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abstract = "5-Deoxy-5-iodo-1,2-O-isopropylidene-3-O-methyl-α-d-xylofuranose, prepared quantitatively from its 5-O p-tolylsulfonyl precursor, readily gave the 5-C-(diethoxy-phosphinyl) derivative. Treatment of this compound with sodium dihydrobis(2-methoxyethoxy)aluminate, followed by hydrogen peroxide, mineral acid, and hydrogen peroxide, yielded 5-deoxy-5-C-(hydroxyphosphinyl)-3-O-methyl-α,β-d-xylopyranoses in 65{\%} overall yield. The structures of these sugar analogs were effectively established on the basis of the mass and 400-MHz, 1H-n.m.r. spectra of the four title compounds, derived by treatment with diazomethane and then acetic anhydride in pyridine. 5-C-[(S)-(1-Acetoxyethenyl)phosphino]-1,2,4-tri-O-acetyl-5-deoxy-3-O-methyl-β-d-xylopyranose was also isolated and characterized.",
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N2 - 5-Deoxy-5-iodo-1,2-O-isopropylidene-3-O-methyl-α-d-xylofuranose, prepared quantitatively from its 5-O p-tolylsulfonyl precursor, readily gave the 5-C-(diethoxy-phosphinyl) derivative. Treatment of this compound with sodium dihydrobis(2-methoxyethoxy)aluminate, followed by hydrogen peroxide, mineral acid, and hydrogen peroxide, yielded 5-deoxy-5-C-(hydroxyphosphinyl)-3-O-methyl-α,β-d-xylopyranoses in 65% overall yield. The structures of these sugar analogs were effectively established on the basis of the mass and 400-MHz, 1H-n.m.r. spectra of the four title compounds, derived by treatment with diazomethane and then acetic anhydride in pyridine. 5-C-[(S)-(1-Acetoxyethenyl)phosphino]-1,2,4-tri-O-acetyl-5-deoxy-3-O-methyl-β-d-xylopyranose was also isolated and characterized.

AB - 5-Deoxy-5-iodo-1,2-O-isopropylidene-3-O-methyl-α-d-xylofuranose, prepared quantitatively from its 5-O p-tolylsulfonyl precursor, readily gave the 5-C-(diethoxy-phosphinyl) derivative. Treatment of this compound with sodium dihydrobis(2-methoxyethoxy)aluminate, followed by hydrogen peroxide, mineral acid, and hydrogen peroxide, yielded 5-deoxy-5-C-(hydroxyphosphinyl)-3-O-methyl-α,β-d-xylopyranoses in 65% overall yield. The structures of these sugar analogs were effectively established on the basis of the mass and 400-MHz, 1H-n.m.r. spectra of the four title compounds, derived by treatment with diazomethane and then acetic anhydride in pyridine. 5-C-[(S)-(1-Acetoxyethenyl)phosphino]-1,2,4-tri-O-acetyl-5-deoxy-3-O-methyl-β-d-xylopyranose was also isolated and characterized.

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