741686-50-0

Basic information

• Product Name: 1,2-anhydro-3,5-di-O-(4-methylbenzoyl)-2-C-methyl-β-D-ribofuranose
• Synonyms: 1,2-anhydro-3,5-di-O-(4-methylbenzoyl)-2-C-methyl-β-D-ribofuranose
• CAS NO: 741686-50-0
• Molecular Weight: 382.413
• Mol File: 741686-50-0.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 1,2-anhydro-3,5-di-O-(4-methylbenzoyl)-2-C-methyl-β-D-ribofuranose(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-anhydro-3,5-di-O-(4-methylbenzoyl)-2-C-methyl-β-D-ribofuranose(741686-50-0)
• EPA Substance Registry System: 1,2-anhydro-3,5-di-O-(4-methylbenzoyl)-2-C-methyl-β-D-ribofuranose(741686-50-0)

Safety Data

• Hazardous Substances Data: 741686-50-0(Hazardous Substances Data)

Upstream product

• 55533-86-3 3-O-benzyl-3-C-methyl-1,2-O-isopropylidene-α-D-allofuranose 
• 943638-20-8 2-C-methyl-3,5-di-O-(4-methylbenzoyl)-D-ribofuranose 

Downstream Products

• 1338072-45-9 4-chloro-7-[2-C-methyl-3,5-di-O-(4-methylbenzoyl)-β-D-ribofuranosyl]-7H-pyrrolo[2,3-d]pyrimidine 
• 1338072-46-0 7-(2-C-methyl-β-D-ribofuranosyl)-4-(phenyl)-7H-pyrrolo[2,3-d]pyrimidine 
• 892389-00-3 4-chloro-5-fluoro-7-(2-C-methyl-3,5-di-O-(p-toluoyl)-β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine 
• 443642-29-3 7-deaza-2'-C-methyl-adenosine 

Relevant articles and documents

Sugar-modified derivatives of cytostatic 6-(het)aryl-7-deazapurine nucleosides: 2′-c-methylribonucleosides, arabinonucleosides and 2′-deoxy-2′-fluoroarabinonucleosides

A series of novel sugar-modified derivatives of cytostatic 6-hetaryl-7-deazapurine ribonucleo-sides: 2′-C-methylribonucleosides, arabinonucleosides and 2′-deoxy-2′-fluoroarabinonucleo-sides bearing an alkyl, aryl and hetaryl group in position 6 were prepared by palladium catalyzed cross-coupling reactions of corresponding (protected) 6-chloro-(7-fluoro)-7-deazapurine nucleosides with (het)arylboronic, hetarylstannanes and trimethylaluminium eventually followed by deprotection. Key intermediate 6-chloro-7-deazapurine 2′-C-methyl-β-D-ribofuranoside was prepared via a stereoselective nucleobase anion glycosylation with toluoyl-protected 1,2-anhydro-2-C-methylribofuranose. The 1,2-anhydro sugar was synthesized in 3 steps starting from readily available 2-C-methylribonolactone. The 6-chloro-7-deazapurine arabinofuranoside intermediate was obtained by epimerization from 3′,5′-protected 6-chloro-7-deazapurine ribofuranoside via 2′-hydroxyl oxidation followed by reduction. None of the prepared compounds showed any considerable cytostatic or antiviral activity.

Practical synthesis of a potent hepatitis C virus RNA replication inhibitor

A practical, efficient synthesis of 1, a hepatitis C virus RNA replication inhibitor, is described. Starting with the inexpensive diacetone glucose, the 12-step synthesis features a novel stereoselective rearrangement to prepare the key crystalline furanose diol intermediate. This is followed by a highly selective glycosidation to couple the C-2 branched furanose epoxide with deazapurine.