452949-21-2

Upstream product

• 233266-76-7 (3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole-5-carbaldehyde 
• 287737-62-6 2-((3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)ethanol 
• 287737-63-7 (3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyl-5-vinyltetrahydrofuro[2,3-d][1,3]dioxole 
• 153186-10-8 ((3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanol 
• 108-24-7 acetic anhydride 
• 287737-64-8 2-((3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)ethyl 4-methylbenzenesulfonate 

Downstream Products

• 287737-66-0 3',5'-di-O-benzyl-4'-C-(p-toluenesulfonyloxyethyl)-2'-O-acetyl-5-methyluridine 
• 287737-69-3 3',5'-di-O-benzyl-4'-C-(p-toluenesulfonyloxyethyl)-2'-O-acetyl-uridine 
• 287737-67-1 3',5'-di-O-benzyl-4'-C-(p-toluenesulfonyloxyethyl)-2'-O-acetyl-4-N-benzoylcytidine 
• 287737-68-2 3',5'-di-O-benzyl-4'-C-(p-toluenesulfonyloxyethyl)-2'-O-acetyl-6-N-benzoyladenosine 
• 287737-37-5 3',5'-di-O-benzyl-2'-O,4'-C-ethylene-5-methyluridine 
• 287737-39-7 5'-O-(4,4'-dimethoxytrityl)-2'-O,4'-C-ethylene-5-methyluridine 
• 287737-33-1 2'-O,4'-C-ethylene-4-N-benzoylcytidine 
• 287737-51-3 2'-O,4'-C-ethylene-4-N-benzoyl-5-methylcytidine 
• 287737-46-6 3',5'-di-O-benzyl-2'-O,4'-C-ethyleneuridine 
• 287737-42-2 2'-O,4'-C-ethylene-6-N-benzoyladenosine 
• 287737-32-0 3',5'-di-O-benzyl-2'-O,4'-C-ethylene-4-N-benzoylcytidine 
• 287737-48-8 5'-O-(4,4'-dimethoxytrityl)-2'-O,4'-C-ethyleneuridine 
• 287737-41-1 3',5'-di-O-benzyl-2'-O,4'-C-ethylene-6-N-benzoyladenosine 
• 287737-35-3 5'-O-(4,4'-dimethoxytrityl)-2'-O,4'-C-ethylene-4-N-benzoylcytidine 

Relevant academic research and scientific papers

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.

2′-O,4′-C-ethylene-bridged nucleic acids (ENA): Highly nuclease-resistant and thermodynamically stable oligonucleotides for antisense drug

To develop antisense oligonucleotides, novel nucleosides, 2′-O,4′-C-ethylene nucleosides and their corresponding phosphoramidites, were synthesized as building blocks. The 1H NMR analysis showed that the 2′-O,4′-C-ethylene linkage of these nucleosides restricts the sugar puckering to the N-conformation as well as the linkage of 2′-O,4′-C-methylene nucleosides which are known as bridged nucleic acids (BNA) or locked nucleic acids (LNA). The ethylene-bridged nucleic acids (ENA) showed a high binding affinity for the complementary RNA strand (ΔTm = + 5.2 °C/modification) and were more nuclease-resistant than natural DNA and BNA/LNA. These results indicate that ENA have better properties as antisense oligonucleotides than BNA/LNA.