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 journalArticlepeer-review

12 Citations (Scopus)

Abstract

Treatment of (RS)-3-O-acetyl-5-deoxy-5-(ethylmethoxyphosphinyl)-1,2-O-isopropyUdene-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 and4C1(L) conformations were established by spectroscopy.

Original languageEnglish
Pages (from-to)4790-4793
Number of pages4
JournalJournal of Organic Chemistry
Volume53
Issue number20
DOIs
Publication statusPublished - Sep 1 1988

ASJC Scopus subject areas

  • Organic Chemistry

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