Synthesis of L-beta-3'-deoxy-3',3'-difluoro-4'-thionucleosides

Feng Zheng; Xiao-Hua Zhang; Xiao-Long Qiu; Xingang Zhang; Feng-Ling Qing

doi:10.1021/ol062576k

Synthesis of L-beta-3'-deoxy-3',3'-difluoro-4'-thionucleosides

Org Lett. 2006 Dec 21;8(26):6083-6. doi: 10.1021/ol062576k.

Authors

Feng Zheng¹, Xiao-Hua Zhang, Xiao-Long Qiu, Xingang Zhang, Feng-Ling Qing

Affiliation

¹ Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China.

PMID: 17165935
DOI: 10.1021/ol062576k

Abstract

[Structure: see text] An efficient route to L-beta-3'-deoxy-3',3'-difluoro-4'-thionucleosides, thio-containing analogues of highly bioactive gemcitabine, is described. Our synthesis highlighted the installation of the thioacetyl group in high efficiency and construction of 3-deoxy-3,3-difluorothiofuranose skeleton in a novel method.

Publication types

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

MeSH terms

Models, Molecular
Nuclear Magnetic Resonance, Biomolecular
Thionucleosides / chemical synthesis*

Substances

Thionucleosides