Biocatalytic route to C-4′-spiro-oxetano-xylofuranosyl pyrimidine nucleosides. Issue 6 (2nd November 2018)

• Record Type: Journal Article
• Authors: Rungta, Pallavi; Mangla, Priyanka; Khatri, Vinod; Maity, Jyotirmoy; Prasad, Ashok K.
• Is Part Of: Biocatalysis and biotransformation. Volume 36:Issue 6(2018)
• Page Start: 458
• Page End: 468
• Publication Date: 2018-11-02
• Subjects: Biocatalysis -- regioselective acetylation -- spiro-nucleosides; Enzymes -- Biotechnology -- Periodicals; Enzymes -- Industrial applications -- Periodicals; Biotransformation (Metabolism) -- Periodicals; 660.63
• DOI: 10.1080/10242422.2018.1438416
• Languages: English
• ISSNs: 1024-2422

Abstract

Abstract: A facile access to C -4′-spiro-oxetano-xylofuranosyl nucleosides has been demonstrated for the first time through Lipozyme ® TL IM-mediated regioselective acetylation of one of the primary hydroxyl group over the other primary and secondary hydroxyl groups in 3′- O -benzyl-4′- C -hydroxymethyl- β -D -xylofuranosyl nucleosides. Attempts to optimize a convergent route for these spironucleosides via selective manipulation of hydroxyl groups in 3- O -benzyl-4- C -hydroxymethyl-1, 2- O -isopropylidene-α-D -xylofuranose were unsuccessful. Nevertheless; the present linear biocatalytic route efficiently afforded the C -4′-spiro-oxetanoxylofuranosyl nucleosides T and U in 47 and 38% overall yields, respectively, starting from corresponding furanose diol.