methyl 5-(cyanomethyl)-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)imidazole-4-carboxylate

Base Information

• Chemical Name: methyl 5-(cyanomethyl)-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)imidazole-4-carboxylate
• CAS No.: 58931-20-7
• Molecular Formula: C₃₃H₂₇N₃O₉
• Molecular Weight: 609.592

Synonyms:methyl 5-(cyanomethyl)-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)imidazole-4-carboxylate

Chemical Property of methyl 5-(cyanomethyl)-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)imidazole-4-carboxylate

Chemical Property:

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Technology Process of methyl 5-(cyanomethyl)-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)imidazole-4-carboxylate

There total 3 articles about methyl 5-(cyanomethyl)-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)imidazole-4-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose (6974-32-9) + methyl 5-(cyanomethyl)-1H-imidazole-4-carboxylate (56039-06-6) → methyl 5-(cyanomethyl)-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)imidazole-4-carboxylate (58931-20-7)

Guidance literature:

methyl 5-(cyanomethyl)-1H-imidazole-4-carboxylate; With ammonium sulfate; 1,1,1,3,3,3-hexamethyl-disilazane; for 3h; Heating;

1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose; With tin(IV) chloride; In acetonitrile; at 20 ℃; for 3h;

DOI:10.1002/hlca.200390222

Reference yield:

1,2,3,5-tetra-O-benzoyl-β-D-ribofuranose (22224-38-0) + methyl 5-(cyanomethyl)-1H-imidazole-4-carboxylate (56039-06-6) → methyl 5-(cyanomethyl)-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)imidazole-4-carboxylate (58931-20-7)

Guidance literature:

methyl 5-(cyanomethyl)-1H-imidazole-4-carboxylate; With ammonium sulfate; 1,1,1,3,3,3-hexamethyl-disilazane; Heating;

1,2,3,5-tetra-O-benzoyl-β-D-ribofuranose; With tin(IV) chloride; In acetonitrile;

DOI:10.1055/s-2005-869869

Reference yield:

→ methyl 5-(cyanomethyl)-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)imidazole-4-carboxylate (58931-20-7)

Guidance literature:

Imidazol 5, 1-O-Acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose (6);

DOI:10.1021/ja00422a036

upstream raw materials:

1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

methyl 5-(cyanomethyl)-1H-imidazole-4-carboxylate

1,2,3,5-tetra-O-benzoyl-β-D-ribofuranose

Downstream raw materials:

3-deazaguanosine

1-amino-3-deazaguanosine

1-((2R,3R,4R,5R)-3,4-Bis-benzoyloxy-5-benzoyloxymethyl-tetrahydro-furan-2-yl)-5-(cyano-fluoro-methyl)-1H-imidazole-4-carboxylic acid methyl ester

1-{5'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-O-[tris(1-methylethyl)silyl]-β-D-ribofuranosyl}-4-[(diphenylcarbamoyl)oxy]-N⁶(phenoxyacetyl)-1H-imidazo[4,5-c]pyridin-6-amine

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