(2S)-2-[1-(2,4-Difluoro-5-iodophenyl)-2-deoxy-beta-D-ribofuranos-5-yloxy]-8-methyl-4H-1,3,2-benzodioxaphosphole 2-oxide

Kazue Ohkura; Wei Yan Sun; Koh-ichi Seki; Edward E Knaus; Leonard I Wiebe

doi:10.1107/S0108270104021602

(2S)-2-[1-(2,4-Difluoro-5-iodophenyl)-2-deoxy-beta-D-ribofuranos-5-yloxy]-8-methyl-4H-1,3,2-benzodioxaphosphole 2-oxide

Acta Crystallogr C. 2004 Nov;60(Pt 11):o789-91. doi: 10.1107/S0108270104021602. Epub 2004 Oct 9.

Authors

Kazue Ohkura¹, Wei Yan Sun, Koh-ichi Seki, Edward E Knaus, Leonard I Wiebe

Affiliation

¹ Faculty of Pharmaceutical Sciences, Health Sciences University of Hokkaido, Ishikari-Tobetsu Hokkaido 061-0293, Japan. ohkura@hoku-iryo-u.ac.jp

PMID: 15528820
DOI: 10.1107/S0108270104021602

Abstract

The title compound, C(19)H(18)F(2)IO(6)P, prepared as a potential antiviral and anticancer agent from 3-methylsalicylchlorophosphane and 1-(2,4-difluoro-5-iodophenyl)-2-deoxy-beta-D-ribofuranose, is one of a 1:1 mixture of two diastereomers. The diastereomers differ in their configuration, S or R, at the asymmetric phosphorus center. X-Ray crystallographic analysis of the title compound has determined the absolute configuration at the asymmetric P center to be S.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Antineoplastic Agents / chemistry*
Antiviral Agents / chemistry*
Crystallography, X-Ray
Hydrogen Bonding
Indicators and Reagents
Magnetic Resonance Spectroscopy
Models, Molecular
Molecular Conformation
Monosaccharides / chemistry*
Organophosphorus Compounds / chemistry*

Substances

(2S)-2-(1-(2,4-difluoro-5-iodophenyl)-2-deoxy-beta-D-ribofuranos-5-yloxy)-8-methyl-4H-1,3,2-benzodioxaphosphole 2-oxide
Antineoplastic Agents
Antiviral Agents
Indicators and Reagents
Monosaccharides
Organophosphorus Compounds