2,3,5-Tri-O-benzoyl-beta-D-ribofuranosyl cyanide reacts with methyl acetoacetate and diethyl malonate in the presence of stoichiometric amounts of SnCl4 to give a beta-D-ribofuranosyl-enaminoketoester and a beta-D-ribofuranosyl-enaminodiester, respectively. The beta-D-ribofuranosyl-enaminoketoester was debenzoylated, treated with 2,2-dimethoxypropane and tert-butyl-dimethylsilyl chloride to give the methyl 3-amino-3-(5'-O-tert-butyldimethylsilyl-2',3'-O-isopropylidene-beta-D-ribofuranosyl)-2-acetyl propanoate obtained in good yield together with small amounts of its alpha-anomer. The reactions of the beta-anomer with hydrazine, methyl- and phenylhydrazine carried out under controlled experimental conditions, afforded the pyrazole C-nucleosides in good yields as beta-anomers. (C) 2002 Elsevier Science Ltd. All rights reserved.

Synthesis of pyrazole C-nucleosides via Tin(IV) chloride-promoted reactions of beta-D-ribofuranosyl cyanide with beta-dicarbonyl compounds / M. Manferdini, C. F. Morelli, A. Veronese. - In: TETRAHEDRON. - ISSN 0040-4020. - 58:5(2002), pp. 1005-1010.

Synthesis of pyrazole C-nucleosides via Tin(IV) chloride-promoted reactions of beta-D-ribofuranosyl cyanide with beta-dicarbonyl compounds

C. F. Morelli
Secondo
;
2002

Abstract

2,3,5-Tri-O-benzoyl-beta-D-ribofuranosyl cyanide reacts with methyl acetoacetate and diethyl malonate in the presence of stoichiometric amounts of SnCl4 to give a beta-D-ribofuranosyl-enaminoketoester and a beta-D-ribofuranosyl-enaminodiester, respectively. The beta-D-ribofuranosyl-enaminoketoester was debenzoylated, treated with 2,2-dimethoxypropane and tert-butyl-dimethylsilyl chloride to give the methyl 3-amino-3-(5'-O-tert-butyldimethylsilyl-2',3'-O-isopropylidene-beta-D-ribofuranosyl)-2-acetyl propanoate obtained in good yield together with small amounts of its alpha-anomer. The reactions of the beta-anomer with hydrazine, methyl- and phenylhydrazine carried out under controlled experimental conditions, afforded the pyrazole C-nucleosides in good yields as beta-anomers. (C) 2002 Elsevier Science Ltd. All rights reserved.
β-D-ribofuranosyl cyanide; β-dicarbonyl compounds; Pyrazole C-nucleosides
Settore CHIM/06 - Chimica Organica
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/186932
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