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Synthesis 2002(2): 0253-0259
DOI: 10.1055/s-2002-19805
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Peracylated Derivatives of l-Ribofuranose from d-Ribose and Their Use for the Preparation of β-l-Ribonucleosides

Grigorii G. Sivets, Tatjana V. Klennitskaya, Elena V. Zhernosek, Igor A. Mikhailopulo*
Institute of Bioorganic Chemistry, National Academy of Sciences, 220141 Minsk, Acad. Kuprevicha 5, Belarus
Fax: +375(172)648148; e-Mail: igormikh@iboch.bas-net.by;
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Publication History

Received 6 August 2001
Publication Date:
03 August 2004 (online)

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Abstract

A practical synthesis of peracylated derivatives of β-l-ribofuranose 13-15 from d-ribose was accomplished in 6 steps (total yield: 30-45%). Compound 13 was employed for the preparation of 1-(β-l-ribofuranosyl)thymine (16) and -cytosine (17), which are key intermediates for the preparation of the nucleoside derivatives with β-l-configuration. Simultaneous transformation of 17 into β-l-ddC (19) and β-l-3’dC (20) was studied.

Key words

carbohydrates - steroselective synthesis - acylations - nucleosides

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