220569-98-2

Upstream product

• 220569-96-0 ethyl (R)-3-benzyloxymethyl-3-methyl-4-oxobutyrate 
• 100-53-8 phenylmethanethiol 
• 220569-97-1 3-C-(benzyloxymethyl)-2,3-dideoxy-3-C-methyl-D-glycero-tetrofuranose 

Downstream Products

• 220570-02-5 N-[1-((2S,4S)-4-Benzyloxymethyl-4-methyl-tetrahydro-thiophen-2-yl)-2-oxo-1,2-dihydro-pyrimidin-4-yl]-benzamide 
• 220570-01-4 N-[1-((2R,4S)-4-Benzyloxymethyl-4-methyl-tetrahydro-thiophen-2-yl)-2-oxo-1,2-dihydro-pyrimidin-4-yl]-benzamide 
• 220570-00-3 (S)-4-Benzyloxymethyl-2-benzylsulfanyl-4-methyl-tetrahydro-thiophene 

Relevant academic research and scientific papers

Synthesis of novel 3'-C-methyl-4'-thio apionucleosides via highly enantioselective elaboration of quaternary carbon by [3,3]-sigmatropic rearrangement

Asymmetric synthesis of 3'-C-methyl-4'-thio apionucleosides was accomplished from the chiral intermediate 6. The chirality of quaternary carbon of the key intermediate 6 was transferred from the chirality of secondary allylic alcohol 5 via [3,3]-sigmatropic Claisen rearrangement with high enantiomeric excess (estimated to be 98.5% ee). The thioglycosyl intermediate 11 was condensed with silylated N4-benzoylcytosine followed by deprotection to give the desired nucleoside 12.