Author:

Keywords:

base-pairing properties, enzymatic stability, radical cyclization, oligonucleotides, Science & Technology, Physical Sciences, Chemistry, Organic, Chemistry, BASE-PAIRING PROPERTIES, ENZYMATIC STABILITY, RADICAL CYCLIZATION, OLIGONUCLEOTIDES, 0304 Medicinal and Biomolecular Chemistry, 0305 Organic Chemistry, Organic Chemistry, 3101 Biochemistry and cell biology, 3404 Medicinal and biomolecular chemistry, 3405 Organic chemistry

Abstract:

A straightforward synthesis of the branched chain nucleoside 7 is described. This synthesis involves two stereoselective steps : introduction of the hydroxymethyl group on the sugar is achieved by radical cyclization of the (bromomethyl)dimethylsilyl ether of the allylic alcohol 8; the condensation reaction with thymine as base moiety resulted exclusively in the formation of the alpha anomer.