132336-19-7

Upstream product

• 132436-48-7 1-O-acetyl-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-phenylthio-D-erythro-pentofuranose 
• 18027-23-1 4-(N-trimethylsilylacetamido)-2-trimethylsiloxypyrimidine 
• 149204-36-4 (1S)-1-<<(tert-butyldiphenylsilyl)oxy>methyl>-2,3-dihydrofuran 
• 931-59-9 benzenesulfenyl chloride 
• 102717-29-3 (5S)-5-({[tert-butyl(diphenyl)silyl]oxy}methyl)dihydrofuran-2(3H)-one 
• 882-33-7 diphenyldisulfane 
• 129778-50-3 (3R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-phenylsulfanyl-dihydro-furan-2-one 
• 142495-48-5 (3R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-phenylsulfanyl-tetrahydro-furan-2-ol 
• 201472-26-6 (2R/S,5S)-5-(tert-butyldiphenylsilyloxymethyl)tetrahydrofuran-2-ol 
• 54230-57-8 N⁴-acetyl-O-trimethylsilylcytosine 

Relevant academic research and scientific papers

Stereocontrolled Glycosylations Via Addition of Sulfur Electrophiles to Glycals

The methodology described herein examines the regio- and stereoselectivity of pyrimidine and purine glycosylations of furanoid glycals.The results show that following stereoselective sulfenylation, glycosylation of furanoid glycals, in the presence of SnC

FURANOID GLYCAL AS A STARTING MATERIAL FOR NUCLEOSIDE DERIVATIVES

Furanoid glycal was utilized as starting material for the nucleoside derivatives with the aid of benzenesulfenyl chloride.Condensation reaction with silylated nucleic bases was high in the presence of SnCl4.Electrophilic addition of benzenesulfenyl chloride to the glycal with substituent also proceeded in high stereoselectivity.Phenylthio-substituted nucleoside was used to convert 2',3'-dideoxynucleoside and 2',3'-didehydro-2'3'-dideoxynucleoside.

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