445433-93-2

Upstream product

• 54447-56-2 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-[5-13C]ribose 
• 184000-86-0 N²-acetyl-2',3',5'-tri-O-benzoyl-6-O-diphenylcarbamoyl[5'-13C]guanosine 
• 184000-83-7 methyl 2,3,5-tri-O-benzoyl-D-[5-13C]ribofuranoside 
• 69304-37-6 1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane 

Downstream Products

• 445433-97-6 N²-acetyl-6-O-diphenylcarbamoyl-2'-O-phenoxythiocarbonyl-3',5'-O-1,1,3,3-tetraisopropyldisiloxane-1,3-diyl[5'-13C]guanosine 
• 445434-01-5 N²-acetyl-2'-deoxy-6-O-diphenylcarbamoyl-3',5'-O-1,1,3,3-tetraisopropyldisiloxane-1,3-diyl[5'-13C]guanosine 

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.