132336-18-6

Basic information

• Product Name: 1-<5-O-tert-butyldiphenylsilyl)-2,3-dideoxy-2-phenylthio-α-D-erythro-pentofuranosyl>thymine
• Synonyms: 1-<5-O-tert-butyldiphenylsilyl)-2,3-dideoxy-2-phenylthio-α-D-erythro-pentofuranosyl>thymine
• CAS NO: 132336-18-6
• Molecular Weight: 572.8
• Mol File: 132336-18-6.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 1-<5-O-tert-butyldiphenylsilyl)-2,3-dideoxy-2-phenylthio-α-D-erythro-pentofuranosyl>thymine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-<5-O-tert-butyldiphenylsilyl)-2,3-dideoxy-2-phenylthio-α-D-erythro-pentofuranosyl>thymine(132336-18-6)
• EPA Substance Registry System: 1-<5-O-tert-butyldiphenylsilyl)-2,3-dideoxy-2-phenylthio-α-D-erythro-pentofuranosyl>thymine(132336-18-6)

Safety Data

• Hazardous Substances Data: 132336-18-6(Hazardous Substances Data)

Upstream product

• 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 
• 102717-29-3 (5S)-5-({[tert-butyl(diphenyl)silyl]oxy}methyl)dihydrofuran-2(3H)-one 
• 149204-36-4 (1S)-1-<<(tert-butyldiphenylsilyl)oxy>methyl>-2,3-dihydrofuran 
• 931-59-9 benzenesulfenyl chloride 
• 132436-48-7 1-O-acetyl-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-phenylthio-D-erythro-pentofuranose 
• 7288-28-0 2,4-bis(trimethylsiloxy)-5-methylpyrimidine 

Relevant articles and documents

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

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.

A general method for controlling glycosylation stereochemistry in the synthesis of 2′-deoxyribose nucleosides

Glycosylation reactions of 2-arylsulfinyl-O-acetylribosides6 with silylated thymine11 produce 2′-deoxyribose nucleosides with high β-selectivity. An application of this directing effect in the synthesis of the antiretroviral agent D4T,2, is described. Glycosylation reactions of 2-arylsulfinyl-O-acetylribosideswith silylated thymine produce 2′-deoxyribose nucleosides with high β-selectivity. An application of this directing effect in the synthesis of the antiretroviral agent D4T is described. (Chemical Equation Presented).