Synthesis of 3′-azido/-amino-xylobicyclonucleosides. Issue 21 (11th February 2016)

• Record Type: Journal Article
• Authors: Kumar, Manish; Kumar, Rajesh; Rana, Neha; Prasad, Ashok K.
• Is Part Of: RSC advances. Volume 6:Issue 21(2016)
• Page Start: 17713
• Page End: 17719
• Publication Date: 2016-02-11
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/c5ra25222a
• Languages: English
• ISSNs: 2046-2069

Abstract

Abstract : Lipozyme® TL IM mediated the selective deacetylation of one of the two acetoxy groups in 4- C -acetoxymethyl-5- O -acetyl-3-azido-3-deoxy-1, 2- O -isopropylidene-α- d -xylofuranose, leading to the first efficient syntheses of 3′-azido/3′-amino-xylobicyclonucleosides T, U, C and A. Abstract : Lipozyme® TL IM has mediated the selective deacetylation of one of the two diastereotopic acetoxy groups in 4- C -acetoxymethyl-5- O -acetyl-3-azido-3-deoxy-1, 2- O -isopropylidene-α-d -xylofuranose, which led to the first efficient synthesis of 3′-azido/3′-amino-xylobicyclonucleosides T, U, C and A from diacetone-d -glucose, in overall yields of 30 to 35%. Single crystal X-ray study on the compound obtained by the tosylation of the lipase-mediated monodeacetylated sugar unambiguously confirmed the point of diastereoselection on the diacetoxy-sugar derivative. The synthesized bicyclic nucleosides have potential application in antisense/aptamer-based oligonucleotide therapeutics development.