Synthesis of [5'-13C]ribonucleosides and 2'-deoxy[5'-13C]ribonucleosides

The present efficient synthesis of 5'-13C]ribonucleosides and 2'-deoxy5'-13C]ribonucleosides is characterized by the synthesis of the D-5-13C]ribose derivative as an intermediate via the Wittig reaction of 4-aldehydo-D-erythrose dialkyl acetals with Ph3P13CH3I-BuLi to introduce the 13C label at the 5-position of a pentose. This was followed by the highly diastereoselective osmium dihydroxylation for the preparation of 2,3-di-O-benzyl-D-5-13C]ribose dialkyl acetal and the cyclization from D-5-13C]ribose dialkyl acetal derivatives to the alkyl D-5-13C]ribofuranoside derivative by the use of LiBF(4). The obtained D-5-13C]ribose derivative was converted into 5'-13C]ribonucleosides and subsequently into the corresponding 2'-deoxynucleosides.