194656-62-7

Basic information

• Product Name: 1-{3,5-Di-O-benzoyl-2-deoxy-4-C-[(acetylsulfanyl)methyl]-β-D-erythro-pentofuranosyl}uracil
• Synonyms: 1-{3,5-Di-O-benzoyl-2-deoxy-4-C-[(acetylsulfanyl)methyl]-β-D-erythro-pentofuranosyl}uracil
• CAS NO: 194656-62-7
• Molecular Weight: 524.551
• Mol File: 194656-62-7.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 1-{3,5-Di-O-benzoyl-2-deoxy-4-C-[(acetylsulfanyl)methyl]-β-D-erythro-pentofuranosyl}uracil(CAS DataBase Reference)
• NIST Chemistry Reference: 1-{3,5-Di-O-benzoyl-2-deoxy-4-C-[(acetylsulfanyl)methyl]-β-D-erythro-pentofuranosyl}uracil(194656-62-7)
• EPA Substance Registry System: 1-{3,5-Di-O-benzoyl-2-deoxy-4-C-[(acetylsulfanyl)methyl]-β-D-erythro-pentofuranosyl}uracil(194656-62-7)

Safety Data

• Hazardous Substances Data: 194656-62-7(Hazardous Substances Data)

Upstream product

• 194656-38-7 Benzoic acid (2S,3S,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-furan-2-ylmethyl ester 
• 193822-73-0 Benzoic acid (2R,3S,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-2-hydroxymethyl-tetrahydro-furan-2-ylmethyl ester 
• 98-88-4 benzoyl chloride 
• 34832-35-4 sodium thioacetate 
• 183106-52-7 1-{3-O-Benzoyl-4-C-[(benzoyloxy)methyl]-2-deoxy-5-O-p-toluenesulfonyl-α-L-threo-pentofuranosyl}uracil 

Relevant articles and documents

Preparation of chloro and sulfanyl derivatives of 1-(2-deoxy-4-C-hydroxymethyl-α-L-threo-pentofuranosyl)uracil

3′-Chloro and 3′-acetylsulfanyl derivatives of 1-(2-deoxy-4-C-hydroxymethyl-α-L-threo-pentofuranosyl)uracil were prepared by reaction of 2,3′-anhydro-1-{5′-O-benzoyl-4′-C-[(benzoyloxy)methyl]- 2′-deoxy-α-L-erythro-pentofuranosyl}uracil (3) with hydrogen chloride and thioacetic acid, respectively. The reaction with hydrogen chloride gave a mixture of N-1 and N-3 substituted uracil derivatives 12 and 14. Reaction of 1-{3-O-benzoyl-4-C-[(benzoyloxy)methyl]-2-deoxy-α-L-threo-pentofuranosyl} uracil (7) with thionyl chloride and subsequent debenzoylation afforded 1-(4-C-chloromethyl-2-deoxy-β-D-erythro-pentofuranosyl)uracil (19). Nucleophilic substitution with lithium thioacetate, followed by deacylation, converted 1-(3-O-benzoyl-4-C-[(benzoyloxy)methyl]-2-deoxy-5-O-p-toluenesulfonyl-α-L- threo-pentofuranosyl}uracil (9) into 1-(2-deoxy-4-C-sulfanylmethyl-β-D-erythro-pentofuranosyl)uracil (21). The obtained thiols were oxidized with iodine or air to give 1,1′-[disulfandiylbis(2,3-dideoxy-4-hydroxymethyl-α-L-threo- pentofuranose-3, 1-diyl]di(pyrimidine-2,4-(1H,3H)-dione) (17) and 1,1′-[disulfandiylbis(2,5-dideoxy-4-hydroxymethyl-α-L-threo- pentofuranose-5,1-diyl]di(pyrimidine-2,4(1H,3W)-dione) (22). Reaction of 1-(3-acetylsulfanyl-5-O-methanesulfonyl-4-C-[(benzoyloxy)methyl]-2,3-dideoxy- α-L-threo-pentofuranosyl)}uracil (24) with methanolic sodium methoxide afforded 1-(3,5-anhydro-2,3-dideoxy-4-C-hydroxymethyl-3-sulfanyl-α-L-threo- pentofuranosyl)uracil (25). The same reagent was used in the preparation of 1-(3,5-anhydro-2-deoxy-4-C-hydroxymethyl-α-L-threo-pentofuranosyl)uracil (26) from 1-(4-C-[(benzoyloxy)methyl]-2-deoxy-5-O-p-tuluenesulfonyl-α-L-threo- pentofuranosyl}uracil (8). From the series of 4′-substituted 2′-deoxyuridine derivatives, synthesized in this study, solely the 4′-chloromethyl derivative 19 and the oxetane derivative 26 exhibited an appreciable activity against HIV-1 and HIV-2.