Download PDF
Synthesis 2006(1): 73-80  
DOI: 10.1055/s-2005-918451
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of New 1′(N)-Homocarbanucleosides Based on 1-Methylcyclopenta[c]pyrazole Scaffold

Marcos D. García, Olga Caamaño*, Franco Fernández, Paula Abeijon, José Manuel Blanco
Departamento de Química Orgánica, Facultade de Farmacia, Universidade de Santiago de Compostela, 15782 Santiago de Compostela, Spain
Fax: +34(981)594912; e-Mail: qoolga@usc.es;
Further Information

Publication History

Received 20 June 2005
Publication Date:
27 October 2005 (online)

    Permissions and Reprints All articles of this category

Abstract

A series of 1′-homocarbanucleosides was prepared by coupling a purine or pyrimidine to, or constructing it on, a protected 1-methylcyclopenta[c]pyrazole pseudosugar synthesized from (±)-(exo,exo)-1-methyl-4,5,6,7-tetrahydro-4,7-methanoindazole-5,6-diol by oxidative cleavage of the starting glycol, reduction of the resulting dialdehyde with NaBH4, and the protective monosilylation of the bis(hydroxymethyl) reduction product.

Key words

methanoindazoles - 1′(N)-homocarbanucleosides - nucleoside analogues - methylcyclopenta[c]pyrazol - glycol cleavage - silyl ethers

20

The crystallographic data of 9b and 17b have been deposited at the Cambridge Crystallographic Data Centre as supplementary publications numbers CCDC 269757 and 269758. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK.