A shortcut and stereoselective synthesis of 1-β-alkyl-2-deoxy-D-ribose derivatives via Wittig-Horner-Emmons reaction

Naoko Matsuura; Yoshitaka Yashiki; Shouji Nakashima; Minoru Maeda; Shigeki Sasaki

doi:10.3987/com-99-8499

A shortcut and stereoselective synthesis of 1-β-alkyl-2-deoxy-D-ribose derivatives via Wittig-Horner-Emmons reaction

Naoko Matsuura, Yoshitaka Yashiki, Shouji Nakashima, Minoru Maeda, Shigeki Sasaki

Chemo-Pharmaceutical Sciences

Research output: Contribution to journal › Article › peer-review

15 Citations (Scopus)

Abstract

A shortcut and stereoselective synthesis of 1-β-alkyl-2-deoxy-D-ribose derivatives has been achieved via Wittig-Horner-Emmons reaction followed by intramolecular 1,4-addition. After the systematic investigation of the effects of the base and the solvent, the best β-selectivity, as much as 12:1, was obtained with potassium tert-butoxide in THF.

Original language	English
Pages (from-to)	975-978
Number of pages	4
Journal	Heterocycles
Volume	51
Issue number	5
DOIs	https://doi.org/10.3987/com-99-8499
Publication status	Published - May 1 1999

All Science Journal Classification (ASJC) codes

Analytical Chemistry
Pharmacology
Organic Chemistry

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AU - Yashiki, Yoshitaka

AU - Nakashima, Shouji

AU - Maeda, Minoru

AU - Sasaki, Shigeki

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N2 - A shortcut and stereoselective synthesis of 1-β-alkyl-2-deoxy-D-ribose derivatives has been achieved via Wittig-Horner-Emmons reaction followed by intramolecular 1,4-addition. After the systematic investigation of the effects of the base and the solvent, the best β-selectivity, as much as 12:1, was obtained with potassium tert-butoxide in THF.

AB - A shortcut and stereoselective synthesis of 1-β-alkyl-2-deoxy-D-ribose derivatives has been achieved via Wittig-Horner-Emmons reaction followed by intramolecular 1,4-addition. After the systematic investigation of the effects of the base and the solvent, the best β-selectivity, as much as 12:1, was obtained with potassium tert-butoxide in THF.

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A shortcut and stereoselective synthesis of 1-β-alkyl-2-deoxy-D-ribose derivatives via Wittig-Horner-Emmons reaction

Abstract

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