188413-93-6

Basic information

• Product Name: 1,2,3,5-tetra-O-benzoyl-2-C-trimethylsilylethynyl-β-D-ribofuranose
• Synonyms: 1,2,3,5-tetra-O-benzoyl-2-C-trimethylsilylethynyl-β-D-ribofuranose
• CAS NO: 188413-93-6
• Molecular Weight: 662.768
• Mol File: 188413-93-6.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 1,2,3,5-tetra-O-benzoyl-2-C-trimethylsilylethynyl-β-D-ribofuranose(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3,5-tetra-O-benzoyl-2-C-trimethylsilylethynyl-β-D-ribofuranose(188413-93-6)
• EPA Substance Registry System: 1,2,3,5-tetra-O-benzoyl-2-C-trimethylsilylethynyl-β-D-ribofuranose(188413-93-6)

Safety Data

• Hazardous Substances Data: 188413-93-6(Hazardous Substances Data)

Upstream product

• 1066-54-2 trimethylsilylacetylene 
• 157037-56-4 1,3,5-tri-O-benzoyl-2-oxo-α-D-erythro-pentofuranose 

Downstream Products

• 188413-87-8 N⁴-acetyl-2',3',5'-tri-O-benzoyl-2'-C-[(trimethylsilyl)ethynyl]cytidine 
• 188413-96-9 2',3',5'-tri-O-benzoyl-2'-C-[(trimethylsilyl)ethynyl]uridine 

Relevant articles and documents

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.