126049-66-9

Upstream product

• 54230-57-8 N⁴-acetyl-O-trimethylsilylcytosine 
• 129778-50-3 (3R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-phenylsulfanyl-dihydro-furan-2-one 
• 102717-29-3 (5S)-5-({[tert-butyl(diphenyl)silyl]oxy}methyl)dihydrofuran-2(3H)-one 
• 142495-48-5 (3R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-phenylsulfanyl-tetrahydro-furan-2-ol 
• 132336-20-0 N⁴-acetyl-1-<5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-phenylthio-β-D-erythro-pentofuranosyl>cytosine 
• 132336-23-3 N-{1-[(2R,3R,5S)-3-Benzenesulfinyl-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-acetamide 

Relevant academic research and scientific papers

SYNTHESIS OF 2',3'-DIDEHYDRO-2',3'-DIDEOXYNUCLEOSIDES UTILIZING COUPLING REACTIONS BETWEEN NUCLEIC BASES AND PHENYLTHIOSUBSTITUTED 2,3-DIDEOXYRIBOSE

Stereoselectivities in coupling reactions between silylated pyrimidine bases and 3- or 2-α-phenylthio-2,3-dideoxyribose were examined.In the former case, no stereoselectivies were observed when the coupling reactions were performed either with 1-chlorosugar in an SN2 mode or in the presence of Lewis acids as catalyst in an SN1 mode.Coupling reaction with 2-α-phenylthio-2,3-dideoxyribose in the presence of Lewis acids, especially SnCl4, proceeded with good stereoselectivity to give anomeric mixtures of α : β = 1 : 9.All these nucleosides were converted to 2',3'-didehydro-2',3'-dideoxynucleosides by oxidation to sulfoxides followed by thermal elimination of sulfenic acid.

Stereoselectivity in the Coupling Reaction between 2-Phenylthio-2,3-dideoxyribose and Silylated Pyrimidine Bases

Coupling reaction between 2-α-phenylthio-2,3-dideoxyribose and silylated pyrimidine bases in the presence of SnCl4 proceeded stereoselectively to give the β-anomers.These nucleosides were converted to 2',3'-dideoxy-2',3'-didehydronucleosides by oxidation