445462-80-6

Upstream product

• 445433-86-3 2,3-di-O-benzyl-D-ribose dimethyl acetal 
• 138535-81-6 4,5-di-O-acetyl-2,3-di-O-benzyl-D-ribose diethyl dithio acetal 
• 445433-88-5 2,3-di-O-benzyl-4,5-didehydro-4,5-dideoxy-D-[5-13C]ribose dimethyl acetal 
• 445433-87-4 4-aldehydo-2,3-di-O-benzyl-D-erythrose dimethyl acetal 

Relevant academic research and scientific papers

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

The present efficient synthesis of [5'-13C]ribonucleosides and 2'-deoxy[5'-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.