293751-32-3

Basic information

• Product Name: ((1R,3R,4R,7S)-3-(6-benzamido-9H-purin-9-yl)-7-(benzyloxy)-2,5-dioxabicyclo[2.2.1]heptan-1-yl)methyl methanesulfonate
• Synonyms: ((1R,3R,4R,7S)-3-(6-benzamido-9H-purin-9-yl)-7-(benzyloxy)-2,5-dioxabicyclo[2.2.1]heptan-1-yl)methyl methanesulfonate
• CAS NO: 293751-32-3
• Molecular Weight: 551.58
• Mol File: 293751-32-3.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: ((1R,3R,4R,7S)-3-(6-benzamido-9H-purin-9-yl)-7-(benzyloxy)-2,5-dioxabicyclo[2.2.1]heptan-1-yl)methyl methanesulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: ((1R,3R,4R,7S)-3-(6-benzamido-9H-purin-9-yl)-7-(benzyloxy)-2,5-dioxabicyclo[2.2.1]heptan-1-yl)methyl methanesulfonate(293751-32-3)
• EPA Substance Registry System: ((1R,3R,4R,7S)-3-(6-benzamido-9H-purin-9-yl)-7-(benzyloxy)-2,5-dioxabicyclo[2.2.1]heptan-1-yl)methyl methanesulfonate(293751-32-3)

Safety Data

• Hazardous Substances Data: 293751-32-3(Hazardous Substances Data)

Upstream product

• 57099-04-4 3-O-benzyl-1,2-O-isopropylidene-α-D-allofuranose 
• 22331-21-1 1,2:5,6-di-O-isopropylidene-3-O-benzyl-α-D-allofuranose 
• 100-39-0 benzyl bromide 
• 293751-18-5 1-(2-O-acetyl-3-O-benzyl-4-C-methanesulfonoxymethyl-5-O-methanesulfonyl-β-D-erythro-pentofuranosyl)-6-N-benzoyladenine 
• 293751-03-8 1,2-di-O-acetyl-3-O-benzyl-4-C-methanesulfonyloxymethyl-5-O-methanesulfonyl-D-erythro-pentofuranose 
• 293751-01-6 3-O-benzyl-4-C-methanesulfonoxymethyl-5-methanesulfonyl-1,2-O-isopropylidene-α-D-erythro-pentofuranose 
• 63593-03-3 1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose 
• 4005-49-6 N-benzoyladenine 

Downstream Products

• 293751-34-5 ((1S,3R,4R,7R)-3-(6-amino-9H-purin-9-yl)-7-(benzyloxy)-2,5-dioxa-bicyclo-[2.2.1]heptan-1-yl)methanol 
• 209968-94-5 (1S,3R,4R,7S)-3-(6-N-benzoyladenine-9-yl)-7-hydroxy-1-hydroxymethyl-2,5-dioxabicyclo[2.2.1]heptane 
• 206055-70-1 (1S,3R,4R,7S)-3-(6-amino-9H-purin-9-yl)-1-(hydroxymethyl)-2,5-dioxabicyclo[2.2.1]heptan-7-ol 
• 293751-33-4 ((1R,3R,4R,7S)-3-(6-benzamido-9H-purin-9-yl)-7-(benzyloxy)-2,5-dioxabicyclo[2.2.1]heptan-1-yl)methylbenzoate 

Relevant articles and documents

Synthesis of 2′-O,4′-C-alkylene-bridged ribonucleosides and their evaluation as inhibitors of HCV NS5B polymerase

The synthesis of 2′-O,4′-C-methylene-bridged bicyclic guanine ribonucleosides bearing 2′-C-methyl or 5′-C-methyl modifications is described. Key to the successful installation of the methyl functionality in both cases was the use of a one-pot oxidation-Grignard procedure to avoid formation of the respective unreactive hydrates prior to alkylation. The 2′-C-methyl- and 5′-C-methyl-modified bicyclic guanosines were evaluated, along with the known uracil-, cytosine-, adenine-, guanine-LNA and guanine-ENA nucleosides, as potential antiviral agents and found to be inactive in the hepatitis C virus (HCV) cell-based replicon assay. Examination of the corresponding nucleoside triphosphates, however, against the purified HCV NS5B polymerase indicated that LNA-G and 2′-C-methyl-LNA-G are potent inhibitors of both 1b wild type and S282T mutant enzymes in vitro. Activity was further demonstrated for the LNA-G-triphosphate against HCV NS5B polymerase genotypes 1a, 2a, 3a and 4a. A phosphorylation by-pass prodrug strategy may be required to promote anti-HCV activity in the replicon assay.

IMPROVED SYNTHESIS OF ?2.2.1|BICYCLO NUCLEOSIDES

A synthesis of [2.2.1]bicyclo nucleosides which is shorter and provides higher overall yields proceeds via the key intermediate of the general formula III, wherein R4 and R5 are, for instance, sulfonates and R7 is, for instance, a halogen or an acetate. F