Synthesis of 2,2' -anhydro-2 -hydroxy- and 6,2'-anhydro- 6-hydroxy-1-β-d-arabinofuranqsylniootinamide as conpokmationally restricted nicotinamide nucleoside analogs

Krzysztof W. Pankiewicz, Lech A. Ciszewski, Anna T. Ptak

Research output: Contribution to journalArticle

4 Scopus citations

Abstract

1-(β-D-Ribofuranosyl)-2 (1H)-pyridone-3-carboxamide (6a) and the 6(1H)-pyridone derivative (6b) were prepared by condensation of 1,2,3,5-tetra-CHacetyl-/?-D-ribofuranose (3) with 2- and 6-hydroxynicotinic acid, respectively, to 4a and 4b, followed by conversion of the carboxylic acid function of 4a, b into their corresponding carboxamides 5, and then deprotection of 5. Both 6a and 6b were then treated with 1,3-dichloro-1,1,3,3-tetraisopropyldisiloxane to give the corresponding 3', 5'-O-TPDS derivatives, 7a and 7b. Mesylation of 7a,b with mesyl chloride in pyridine afforded the stable, protected mesylates 8a,b. Upon de-O-silylation of 8a,b with Et3NHF gave a mixture of unprotected mesylates 9a,b and 2,2-anhydro- and 6,21-anhydronucleosides, la and lb. Upon storage of 9a,b at room temperature, they are quantitatively converted into la,b. Mild alkaline hydrolysis of la,b afforded their corresponding arabino nucleosides 10a, b.

Original languageEnglish (US)
Pages (from-to)1333-1344
Number of pages12
JournalNucleosides and Nucleotides
Volume10
Issue number6
DOIs
StatePublished - Sep 1 1991

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