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Synthesis 2002(12): 1652-1654
DOI: 10.1055/s-2002-33639
SHORTPAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of 1,4-Anhydro-2-deoxy-d-ribitol Derivatives from Thymidine Using Improved Preparation of Furanoid Glycals

Vladimir Serebryany, Alexander Karpeisky, Jasenka Matulic-Adamic, Leonid Beigelman*
Department of Organic Chemistry, Ribozyme Pharmaceuticals Inc., 2950 Wilderness Place, Boulder, CO 80301, USA
Fax: +1(303)4496995; e-Mail: lnb@rpi.com;
Further Information

Publication History

Received 25 March 2002
Publication Date:
05 September 2002 (online)

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Abstract

Preparation of furanoid glycal by elimination of the nucleobase from thymidine has been investigated. A number of catalysts for this reaction were tested, resulting in improved and scaleable synthesis. Hydrogenation of the resulting glycal afforded the 5-protected 1,4-anhydro-2-deoxy-d-ribitol derivative in a high yield.

Keywords

carbohydrates - furans - glycals - thymidine - hydrogenation - nucleosides

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