156475-03-5

Basic information

• Product Name: [(2R,3S,4S)-3,4-dihydroxytetrahydro-2-furanyl]methyl benzoate
• Synonyms: [(2R,3S,4S)-3,4-dihydroxytetrahydro-2-furanyl]methyl benzoate
• CAS NO: 156475-03-5
• Molecular Weight: 238.24
• Mol File: 156475-03-5.mol

Chemical Properties

• CAS DataBase Reference: [(2R,3S,4S)-3,4-dihydroxytetrahydro-2-furanyl]methyl benzoate(CAS DataBase Reference)
• NIST Chemistry Reference: [(2R,3S,4S)-3,4-dihydroxytetrahydro-2-furanyl]methyl benzoate(156475-03-5)
• EPA Substance Registry System: [(2R,3S,4S)-3,4-dihydroxytetrahydro-2-furanyl]methyl benzoate(156475-03-5)

Safety Data

• Hazardous Substances Data: 156475-03-5(Hazardous Substances Data)

Upstream product

• 4099-85-8 methyl 2,3-O-isopropylidene-D-ribofuranoside 
• 313484-66-1 (3R,4R,5R)-2-Methoxy-3,4-bis-trimethylsilanyloxy-5-trimethylsilanyloxymethyl-tetrahydro-furan 
• 532-20-7 D-Ribose 
• 1824-96-0 methyl ribofuranoside 
• 268545-16-0 5-O-benzoyl-2,3-isopropylidene-1-methoxy-D-ribofuranoside 
• 98-88-4 benzoyl chloride 
• 491-19-0 1,4-anhydro-D-ribitol 

Downstream Products

• 268545-18-2 (3S,4R,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydro-3-furanyl 4-methylbenzenesulfonate 

Relevant articles and documents

Benzimidazole 2'-isonucleosides: Design, synthesis, and antiviral activity of 2-substituted-5,6-dichlorobenzimidazole 2'-isonucleosides

2,5,6-Trihalogenated benzimidazole-β-D-ribofuranosyl nucleosides and 2- substituted amino-5,6-dichlorobenzimidazole-β-L-ribofuranosyl nucleosides are potent and selective inhibitors of human cytomegalovirus (HCMV). The D- ribofuranosyl analogs are metabolized rapidly in vivo rendering them unsuitable as drug candidates. The primary source of instability is thought to be the anomeric bond. The synthesis of a series of chemically stable benzimidazole-2'-isonucleosides is presented. The synthetic schemes employed are based on nucleophilic displacements of a 2'-tosylate from carbohydrate intermediates with 2-bromo-5,6-dichlorobenzidazole. 2-Bromo and 2-isopropyl amino analogs with 3'- and 5'-oxo and deoxy substitutions were prepared. The benzimidazole-2'-isonucleosides presented here demonstrated reduced activity against HCMV when compared to other D-ribofuranosyl benzimidazole analogs. In addition, they were not found to be inhibitors of HIV.

SYNTHESIS OF NOVEL 3'-ISOMERIC DIDEOXYNUCLEOSIDES

Approaches to representative examples of 3'-isomeric dideoxynucleosides with 2'(S),3'(R) and 2'(R),3'(S) absolute stereochemistry have been developed.These are among the first cases of isomeric dideoxynucleosides with the base moiety at the 3'-position.The chemistry developed has generality and can be applied to the synthesis of other related isomeric nucleosides.