1094603-23-2

Basic information

• Product Name: ((1R,3R,4R,7S)-7-(benzyloxy)-3-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dioxabicyclo[2.2.1]heptan-1-yl)methyl benzoate
• Synonyms: ((1R,3R,4R,7S)-7-(benzyloxy)-3-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dioxabicyclo[2.2.1]heptan-1-yl)methyl benzoate
• CAS NO: 1094603-23-2
• Molecular Weight: 450.448
• Mol File: 1094603-23-2.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: ((1R,3R,4R,7S)-7-(benzyloxy)-3-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dioxabicyclo[2.2.1]heptan-1-yl)methyl benzoate(CAS DataBase Reference)
• NIST Chemistry Reference: ((1R,3R,4R,7S)-7-(benzyloxy)-3-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dioxabicyclo[2.2.1]heptan-1-yl)methyl benzoate(1094603-23-2)
• EPA Substance Registry System: ((1R,3R,4R,7S)-7-(benzyloxy)-3-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dioxabicyclo[2.2.1]heptan-1-yl)methyl benzoate(1094603-23-2)

Safety Data

• Hazardous Substances Data: 1094603-23-2(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 
• 1094603-21-0 (2R,3R,4S)-4-(benzyloxy)-2-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-5,5-bis(((methylsulfonyl)oxy)methyl)tetrahydrofuran-3-yl acetate 
• 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 
• 532-32-1 sodium benzoate 
• 1094603-22-1 ((1R,3R,4R,7S)-7-(benzyloxy)-3-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dioxabicyclo[2.2.1]heptan-1-yl)methyl methanesulfonate 

Downstream Products

• 200435-91-2 1-((1S,3R,4R,7S)-7-(benzyloxy)-1-(hydroxymethyl)-2,5-dioxabicyclo[2.2.1]heptan-3-yl)pyrimidine-2,4(1H,3H)-dione 
• 200435-92-3 1-((1S,3R,4R,7S)-7-hydroxy-1-(hydroxymethyl)-2,5-dioxabicyclo[2.2.1]heptan-3-yl)pyrimidine-2,4(1H,3H)-dione 

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.

Optimized synthesis of LNA uracil nucleosides

A short, very high yielding, and practical synthesis of LNA uracil diol 6 has been developed from the easily accessible glycosyl donor 1. The concluding O3′-debenzylation of 5 resulted in significant reduction of the uracil moiety with many typical debenz