Synthesis and structural analysis of 5-deoxy-5-[(RS)-ethylphosphinyl]-α,β-L-idopyranoses

Hiroshi Yamamoto, Tadashi Hanaya, Heizan Kawamoto, Saburo Inokawa

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

Treatment of (5RS)-3-O-acetyl-5-deoxy-5-(ethylmethoxyphosphinyl)-1,2-O-isopropylidene-α -D-xylo-hexofuranose (5) with dihydropyran in dichloromethane containing pyridinium p-toluenesulfonate gave the 6-O-(tetrahydropyran-2-yl) derivative 7 in 90% yield. Reduction of 7 with sodium dihydrobis(2-methoxyethoxy)aluminate followed by acid hydrolysis preponderantly provided the title compounds, the first unsubstituted L-idopyranoses having a phosphinyl group in the hemiacetal ring. These compounds were converted into four separable 1,2,3,4,6-penta-O-acetates 11a-d, whose structures and 4C1 (L) conformations were established by spectroscopy.

Original languageEnglish
Pages (from-to)4790-4793
Number of pages4
JournalJournal of Organic Chemistry
Volume53
Issue number20
Publication statusPublished - 1988

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Methylene Chloride
Structural analysis
Conformations
Hydrolysis
Acetates
Sodium
Spectroscopy
Derivatives
Acids
4-toluenesulfonic acid
propylene
dihydrobis(2-methoxyethoxy)aluminate

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Synthesis and structural analysis of 5-deoxy-5-[(RS)-ethylphosphinyl]-α,β-L-idopyranoses. / Yamamoto, Hiroshi; Hanaya, Tadashi; Kawamoto, Heizan; Inokawa, Saburo.

In: Journal of Organic Chemistry, Vol. 53, No. 20, 1988, p. 4790-4793.

Research output: Contribution to journalArticle

Yamamoto, Hiroshi ; Hanaya, Tadashi ; Kawamoto, Heizan ; Inokawa, Saburo. / Synthesis and structural analysis of 5-deoxy-5-[(RS)-ethylphosphinyl]-α,β-L-idopyranoses. In: Journal of Organic Chemistry. 1988 ; Vol. 53, No. 20. pp. 4790-4793.
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