125440-13-3

Basic information

• Product Name: (S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-trimethylsilanyloxy-2,3-dihydro-furan
• Synonyms: (S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-trimethylsilanyloxy-2,3-dihydro-furan
• CAS NO: 125440-13-3
• Molecular Weight: 426.703
• Mol File: 125440-13-3.mol

Chemical Properties

• CAS DataBase Reference: (S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-trimethylsilanyloxy-2,3-dihydro-furan(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-trimethylsilanyloxy-2,3-dihydro-furan(125440-13-3)
• EPA Substance Registry System: (S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-trimethylsilanyloxy-2,3-dihydro-furan(125440-13-3)

Safety Data

• Hazardous Substances Data: 125440-13-3(Hazardous Substances Data)

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 102717-29-3 (5S)-5-({[tert-butyl(diphenyl)silyl]oxy}methyl)dihydrofuran-2(3H)-one 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 32780-06-6 (5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran 

Downstream Products

• 129778-55-8 (3S,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-phenylsulfanyl-dihydro-furan-2-one 
• 129778-50-3 (3R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-phenylsulfanyl-dihydro-furan-2-one 
• 115728-44-4 5-O-(tert-butyldiphenylsilyl)-3-deoxy-2-Se-phenyl-2-seleno-D-erythro-pentonic acid γ-lactone 
• 129778-54-7 1-[(2R,3R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-(2-nitro-phenylsulfanyl)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione 
• 129778-54-7 1-[(2S,3R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-(2-nitro-phenylsulfanyl)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione 
• 129778-45-6 Acetic acid (3R,5S)-5-(tert-butyl-diphenyl-silanyloxymethyl)-3-(2-nitro-phenylsulfanyl)-tetrahydro-furan-2-yl ester 
• 5983-09-5 2',3'-Dideoxyuridine 
• 4097-22-7 2',3'-Dideoxyadenosine 
• 3056-17-5 stavudin 
• 141684-89-1 6-chloro-2-fluoro-9-<5-O-(tert-butyldiphenylsilyl)-3-deoxy-2-Se-phenyl-2-seleno-β-D-erythro-pentofuranosyl>-9H-purine 
• 141684-89-1 9-[(2S,3R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-phenylselanyl-tetrahydro-furan-2-yl]-6-chloro-2-fluoro-9H-purine 
• 141684-90-4 2-amino-6-chloro-9-<5-O-(tert-butyldiphenylsilyl)-3-deoxy-2-Se-phenyl-2-seleno-β-D-erythro-pentofurnanosyl>-9H-purine 
• 141684-91-5 2-fluoro-9-<5-O-(tert-butyldiphenylsilyl)-3-deoxy-2-Se-phenyl-2-seleno-β-D-erythro-pentofurnanosyl>-9H-adenine 
• 141684-83-5 N⁶-methyl-9-<5-O-(tert-butyldiphenylsilyl)-3-deoxy-2-Se-phenyl-2-seleno-β-D-erythro-pentofuranosyl>adenine 

Relevant articles and documents

Synthesis of nucleosides As a Novel Class of Uridine Phosphorylase Inhibitors

thymine was synthesized and found to be a potent inhibitor of uridine phosphorylase.

A Highly Stereoselective Synthesis of Anti-HIV 2',3'-Dideoxy- and 2',3'-Didehydro-2',3'-dideoxynucleosides

A general total synthesic method for the stereocontrolled synthesis of 2',3'-dideoxy- as well as 2',3'-didehydro-2',3'-dideoxynucleosides is presented.Introduction of an α-phenylselenenyl group at the 2-position of 2,3-dideoxyribosyl acetate directs the glycosyl bond formation to give >/=95percent β-isomer.This 2'-phenylselenenyl nucleoside may be converted to either the 2',3'-dideoxynucleoside by treatment with n-Bu3SnH and Et3B at room temperature or to the unsaturated derivative by treatment with H2O2/cat. pyridine.The application of this method to the syntheses of pyrimidines (ddU, ddT, ddC), 6-substituted purines (ddA, ddI, 6-chloro-ddP, N6-Me-ddA), and 2,6-disubstituted purines (2-F-ddA, 6-chloro-2-amino-ddP) as well as selected 2',3'-didehydro-2',3'-dideoxy derivatives is reported.

Diastereoselective Sulfenylation Reactions Employing N-(Phenylthio)lactams under Nonbasic Conditions

Silyl enol ethers and silyl ketene acetals react with sulfenamides in the presence of trimethylsilyl triflate to give the corresponding trans-sulfenylated ketones and lactones.

A Highly Stereoselective Glycosylation of 2-(Phenylselenenyl)-2,3-dideoxyribose Derivative with Thymine: Synthesis of 3'-Deoxy-2',3'-didehydrothymidine and 3'-Deoxythymidine

A highly stereoselective synthesis of 3'-deoxy-2',3'-didehydrothymidine (D4T) and 3'-deoxythymidine (D2T) was achieved from the condensation of 2-(phenylselenenyl)-2,3-dideoxyribose derivative and silylated thymine in the presence of trimethylsilyl triflate.

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).