125440-17-7

Basic information

• Product Name: Thymidine, 2',3'-didehydro-3'-deoxy-5'-O-[(1,1-dimethylethyl)diphenylsilyl]-
• CAS NO: 125440-17-7
• Molecular Formula: C26H30N2O4Si
• Molecular Weight: 462.621
• Mol File: 125440-17-7.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: Thymidine, 2',3'-didehydro-3'-deoxy-5'-O-[(1,1-dimethylethyl)diphenylsilyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: Thymidine, 2',3'-didehydro-3'-deoxy-5'-O-[(1,1-dimethylethyl)diphenylsilyl]-(125440-17-7)
• EPA Substance Registry System: Thymidine, 2',3'-didehydro-3'-deoxy-5'-O-[(1,1-dimethylethyl)diphenylsilyl]-(125440-17-7)

Safety Data

• Hazardous Substances Data: 125440-17-7(Hazardous Substances Data)

Upstream product

• 129778-51-4 1-<5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-phenylthio-β-D-erythro-pentofuranosyl>thymine 
• 3444-09-5 1,3-bis(trimethylsilyl)thymine 
• 7288-28-0 2,4-bis(trimethylsiloxy)-5-methylpyrimidine 
• 115728-43-3 5-O-(tert-butyldiphenylsilyl)-3-deoxy-2-Se-phenyl-2-seleno-D-threo-pentonic acid γ-lactone 
• 129778-56-9 (3R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-(2-nitro-phenylsulfanyl)-dihydro-furan-2-one 
• 129778-50-3 (3R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-phenylsulfanyl-dihydro-furan-2-one 
• 129778-45-6 Acetic acid (3R,5S)-5-(tert-butyl-diphenyl-silanyloxymethyl)-3-(2-nitro-phenylsulfanyl)-tetrahydro-furan-2-yl ester 
• 142495-48-5 (3R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-phenylsulfanyl-tetrahydro-furan-2-ol 
• 132436-48-7 1-O-acetyl-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-phenylthio-D-erythro-pentofuranose 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 115728-44-4 5-O-(tert-butyldiphenylsilyl)-3-deoxy-2-Se-phenyl-2-seleno-D-erythro-pentonic acid γ-lactone 
• 125440-13-3 (S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-trimethylsilanyloxy-2,3-dihydro-furan 
• 102717-29-3 (5S)-5-({[tert-butyl(diphenyl)silyl]oxy}methyl)dihydrofuran-2(3H)-one 
• 149656-26-8 1-O-acetyl-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-(phenylselenenyl)-D-erythro-pentafuranose 

Downstream Products

• 3056-17-5 stavudin 

Relevant articles and documents

Simple entry to 3'-substituted analogues of anti-HIV agent stavudine based on an anionic O --> C stannyl migration.

Reaction of 5'-O-protected derivatives of the anti-HIV agent stavudine (d4T) with LTMP was investigated with the aim to lithiate the vinylic hydrogens (H-3' and H-2'). When the lithiation of the 5'-O-tert-butyldiphenylsilyl derivative 5 was carried out in the presence of HMPA, an anionic silyl migration took place to give the 3'-C-silylated product 4a. The stannyl version of this reaction was found to be also possible, which has disclosed a highly simple entry to the d4T analogues variously substituted at the 3'-position by manipulating the 3'-C-stannyl d4T as a common intermediate.

Synthesis of 2',3'-didehydro-2',3'-dideoxy nucleosides from 2',2'-bis(phenylthio) nucleoside analogs

2',3'-Didehydro-2',3'-dideoxy nucleosides were synthesized from 2',2'-bis(phenylthio) nucleoside analogs via five-step reactions. The sulfonyl group of the intermediate was removed by a treatment with sodium amalgam.

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.