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 journalArticle

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
Publication statusPublished - Apr 13 2007

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Erythritol
Addition reactions
Skeleton
Sugars
Elongation
Carbon
erythrose
dimethyl hydrogen phosphite
1,4-dioxane

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Hanaya, T., Tsukui, H., Igi, N., Noguchi, A., Kawamoto, H., & Yamamoto, H. (2007). A new route for preparation of 2-deoxy-D-ribofuranose phospho sugar. Heterocycles, 72, 411-420.

A new route for preparation of 2-deoxy-D-ribofuranose phospho sugar. / Hanaya, Tadashi; Tsukui, Hiroyuki; Igi, Naomi; Noguchi, Ayashi; Kawamoto, Heizan; Yamamoto, Hiroshi.

In: Heterocycles, Vol. 72, 13.04.2007, p. 411-420.

Research output: Contribution to journalArticle

Hanaya, T, Tsukui, H, Igi, N, Noguchi, A, Kawamoto, H & Yamamoto, H 2007, 'A new route for preparation of 2-deoxy-D-ribofuranose phospho sugar', Heterocycles, vol. 72, pp. 411-420.
Hanaya T, Tsukui H, Igi N, Noguchi A, Kawamoto H, Yamamoto H. A new route for preparation of 2-deoxy-D-ribofuranose phospho sugar. Heterocycles. 2007 Apr 13;72:411-420.
Hanaya, Tadashi ; Tsukui, Hiroyuki ; Igi, Naomi ; Noguchi, Ayashi ; Kawamoto, Heizan ; Yamamoto, Hiroshi. / A new route for preparation of 2-deoxy-D-ribofuranose phospho sugar. In: Heterocycles. 2007 ; Vol. 72. pp. 411-420.
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AU - Kawamoto, Heizan

AU - Yamamoto, Hiroshi

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