A New Synthetic Approach to Elvucitabine

doi:10.1007/s40242-013-2161-4

Chemical Research in Chinese Universities ›› 2013, Vol. 29 ›› Issue (1): 57-61.doi: 10.1007/s40242-013-2161-4

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A New Synthetic Approach to Elvucitabine

ZHANG Ling-yu¹, LOU Yuan-yuan¹, ZHAO Gui-long^1,2, ZHANG Lin-shan¹, CHEN Yan³

1. Tianjin Key Laboratory of Molecular Design and Drug Discovery, Tianjin Institute of Pharmaceutical Research, Tianjin 300193, P. R. China;
2. School of Chemical and Pharmaceutical Engineering, Shandong Polytechnic Institute, Jinan 250353, P. R. China;
3. Shandong Blood Center, Jinan 250014, P. R. China

Received:2012-04-23 Revised:2012-06-04 Online:2013-02-01 Published:2013-01-23
Supported by:
Supported by the International Collaboration Project of Ministry of Science and Technology, China(No.2012ZX09105102).

Abstract

Abstract:

A new synthetic approach to elvucitabine started from L-xylose via the reactions of 10 steps in an overall yield of 20% was developed. The key steps included trimethylsilyl trifluoromethanesulfonate(TMSOTf)-mediated stereocontrolled β-glycosidation and exquisite choice of chloroacetyl group for the protection of hydroxyl groups as well as the corresponding deprotection under notably mild conditions. The structure of elvucitabine, in particular, the stereochemistry thereof, was unambiguously determined by comparison of the physical properties, such as ¹H NMR data and the specific rotation, of the synthesized sample with those reported.

Key words: Elvucitabine, Antiviral, Nucleoside analogue, Synthetic methodology

ZHANG Ling-yu, LOU Yuan-yuan, ZHAO Gui-long, ZHANG Lin-shan, CHEN Yan. A New Synthetic Approach to Elvucitabine[J]. Chemical Research in Chinese Universities, 2013, 29(1): 57-61.

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A New Synthetic Approach to Elvucitabine

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