16434-52-9

Basic information

• Product Name: C₃₉H₃₁N₅O₈
• Synonyms: C₃₉H₃₁N₅O₈
• CAS NO: 16434-52-9
• Molecular Weight: 697.704
• Mol File: 16434-52-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: C₃₉H₃₁N₅O₈(CAS DataBase Reference)
• NIST Chemistry Reference: C₃₉H₃₁N₅O₈(16434-52-9)
• EPA Substance Registry System: C₃₉H₃₁N₅O₈(16434-52-9)

Safety Data

• Hazardous Substances Data: 16434-52-9(Hazardous Substances Data)

Upstream product

• 4005-49-6 N-benzoyladenine 
• 15397-15-6 1,2,3,5-tetra-O-benzoyl-2-C-methyl-β-D-ribofuranose 
• 15397-15-6 1,2,3,5-Tetra-O-benzoyl-2-C-methyl-α(β)-D-ribofuranose 
• 22224-41-5 1,3,5-tri-O-benzoyl-α-D-ribofuranoside 
• 157037-56-4 1,3,5-tri-O-benzoyl-2-oxo-α-D-erythro-pentofuranose 
• 98-88-4 benzoyl chloride 

Downstream Products

• 15397-12-3 2'-C-methyladenosine 
• 15397-12-3 2'-methyl-adenosine 

Relevant articles and documents

METHODS AND COMPOSITIONS FOR TREATING HEPATITIS C VIRUS

The present invention provides pharmaceutical compositions for the treatment of a hepatitis C infection in a host, comprising an antivirally effective amount of a 2'-C-branched nucleoside or a 2'-C-branched ribofuranosyl nucleoside, or pharmaceutically acceptable salts or esters thereof, in combination with one or more other anti-HCV agent. The present invention further provides the use of a 2'-C-branched nucleoside or a 2'-C-branched ribofuranosyl nucleoside, or pharmaceutically acceptable salts or esters thereof, in the manufacture of a medicament for the treatment of a hepatitis C infection in a host.

A short, flexible route toward 2'-C-branched ribonucleosides

A five-step synthesis of 2'-C-branched ribonucleosides from commercially obtained 1,3,5-tri-O-benzoyl-α-D-ribofuranose (4) is described. The free hydroxyl group of 4 was oxidized in high yield with Dess-Martin periodane reagent. The resultant 2-ketosugar was treated with MeMgBr/TiCl4, CH2=CHMgBr/CeCl3, or TMSC≡CLi/CeCl3, and in each case addition to the ketone proceeded stereoselectively to provide 2-alkylated ribofuranosides. After conversion to the corresponding tetrabenzoyl derivatives, the 2-alkylribofuranosides were coupled to nucleobases under Vorbruggen persilylation conditions, giving the β-nucleosides with high stereoselectivity. Deprotection with methanolic ammonia provided the title compounds in 17-49% overall yields from 4.