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Synthesis 2005(17): 2865-2870  
DOI: 10.1055/s-2005-872204
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of 2′-Deoxy-2′-C-α-methylpurine Nucleosides

Nan-Sheng Li*, Joseph A. Piccirilli*
Howard Hughes Medical Institute, Department of Biochemistry & Molecular Biology and Department of Chemistry, University of Chicago, 5841 S. Maryland Ave., MC 1028, Chicago, IL 60637, USA
Fax: +1(773)7020271; e-Mail: nli@uchicago.edu; e-Mail: jpicciri@uchicago.edu;
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Publication History

Received 15 April 2005
Publication Date:
23 August 2005 (online)

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Abstract

2′-Deoxy-2′-C-α-methylribonucleosides provide valuable biochemical probes with which to study RNA structure and function. Using methyl 2-acetoxymethyl-3,5-di-O-(tert-butyldi­methylsilyl)-d-ribofuranoside (1) as a glycosylating agent, we achieved in four steps an improved synthesis of 2′-deoxy-2′-C-α-methyladenosine (8) and the first synthesis of 2′-deoxy-C-α-methylguanosine (9) in 25% and 17% overall yield, respectively.

Key words

nucleosides - deoxygenation - glycosylation - deoxy­methyladenosine - deoxymethylguanosine

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