A new route for preparation of 2-deoxy-D-ribofuranose phospho sugar

Tadashi Hanaya, Hiroyuki Tsukui, Naomi Igi, Ayashi Noguchi, Heizan Kawamoto, Hiroshi Yamamoto

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)

Abstract

The addition reaction of dimethyl phosphonate to (2R,4S)-4-(tert-butyldimethylsilyl)oxymethyl-2-methyl-1,3-dioxan-5-one (11a), followed by dehydroxylation, provided 1-O-(tert-butyldimethylsilyl)-3-deoxy-3-dimethoxy-phosphinoyl-2,4-O-ethylidene-d-erythritol (13a). Elongation of carbon skeleton of the d-erythrose (14) derived from 13a and then acidic methanolysis gave a mixture of methyl 2,4-dideoxy-4-dimethoxyphosphinoyl-α,β-d-erythro-pentopyranosides (7), which was led to 2-deoxy-D-ribofuranose phospho sugar (4) in an appreciably improved total yield compared with the procedures via previously reported route.

Original languageEnglish
Pages (from-to)411-420
Number of pages10
JournalHeterocycles
Volume72
DOIs
Publication statusPublished - Apr 13 2007

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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