622379-64-0

Basic information

• Product Name: 9-(2',3',5'-tri-O-benzoyl-2'-C-methyl-β-D-ribofuranosyl)-6-methylthio-purine
• Synonyms: 9-(2',3',5'-tri-O-benzoyl-2'-C-methyl-β-D-ribofuranosyl)-6-methylthio-purine
• CAS NO: 622379-64-0
• Molecular Weight: 624.674
• Mol File: 622379-64-0.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 9-(2',3',5'-tri-O-benzoyl-2'-C-methyl-β-D-ribofuranosyl)-6-methylthio-purine(CAS DataBase Reference)
• NIST Chemistry Reference: 9-(2',3',5'-tri-O-benzoyl-2'-C-methyl-β-D-ribofuranosyl)-6-methylthio-purine(622379-64-0)
• EPA Substance Registry System: 9-(2',3',5'-tri-O-benzoyl-2'-C-methyl-β-D-ribofuranosyl)-6-methylthio-purine(622379-64-0)

Safety Data

• Hazardous Substances Data: 622379-64-0(Hazardous Substances Data)

Upstream product

• 50-66-8 6-(methylthio)-1H-purine 
• 15397-15-6 1,2,3,5-tetra-O-benzoyl-2-C-methyl-β-D-ribofuranose 
• 157037-56-4 1,3,5-tri-O-benzoyl-2-oxo-α-D-erythro-pentofuranose 
• 98-88-4 benzoyl chloride 
• 15397-15-6 1,2,3,5-Tetra-O-benzoyl-2-C-methyl-α(β)-D-ribofuranose 
• 50-66-8 6-methylthiopurine 

Downstream Products

• 622379-81-1 C₃₃H₂₈N₄O₉S 

Relevant articles and documents

NUCLEOSIDE DERIVATIVES FOR TREATING HEPATITIS C VIRUS INFECTION

Disclosed are compounds, compositions and methods for treating hepatitis C virus infections.

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.