[4-(2,3,5-tri-O-benzyl-β-D-ribofuranosyl)imidazol-1-yl]methyl 2,2-dimethylpropiolate

Base Information

• Chemical Name: [4-(2,3,5-tri-O-benzyl-β-D-ribofuranosyl)imidazol-1-yl]methyl 2,2-dimethylpropiolate
• CAS No.: 689260-57-9
• Molecular Formula: C₃₅H₄₀N₂O₆
• Molecular Weight: 584.712

Synonyms:[4-(2,3,5-tri-O-benzyl-β-D-ribofuranosyl)imidazol-1-yl]methyl 2,2-dimethylpropiolate

Chemical Property of [4-(2,3,5-tri-O-benzyl-β-D-ribofuranosyl)imidazol-1-yl]methyl 2,2-dimethylpropiolate

Chemical Property:

Purity/Quality:

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Technology Process of [4-(2,3,5-tri-O-benzyl-β-D-ribofuranosyl)imidazol-1-yl]methyl 2,2-dimethylpropiolate

There total 4 articles about [4-(2,3,5-tri-O-benzyl-β-D-ribofuranosyl)imidazol-1-yl]methyl 2,2-dimethylpropiolate 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: 94.0%

Chloromethyl pivalate (18997-19-8) + 4(5)-2,3,5-tri-O-benzyl-β-D-ribofuranosylimidazole (169139-31-5) → [4-(2,3,5-tri-O-benzyl-β-D-ribofuranosyl)imidazol-1-yl]methyl 2,2-dimethylpropiolate (689260-57-9)

Guidance literature:

4(5)-2,3,5-tri-O-benzyl-β-D-ribofuranosylimidazole; With sodium hydride; In tetrahydrofuran; at 20 ℃; for 3h;

Chloromethyl pivalate; In tetrahydrofuran; at 20 ℃; for 1h;

DOI:10.1016/j.tet.2005.09.063

Reference yield:

ethyl 4-(2,3,5-tri-O-benzyl-D-ribofuranosyl)imidazole-1-carboxylate (178381-94-7) → [4-(2,3,5-tri-O-benzyl-β-D-ribofuranosyl)imidazol-1-yl]methyl 2,2-dimethylpropiolate (689260-57-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / aq. NH₄OH / methanol / 3 h / 20 °C

2: 91 percent / NaH / tetrahydrofuran / 5 h / 20 °C

With ammonium hydroxide; sodium hydride; In tetrahydrofuran; methanol;

DOI:10.1016/j.tetlet.2004.01.132

Reference yield:

2,2,2-trichloroethyl 4-(2,3,5-tri-O-benzyl-β-D-ribofuranosyl)imidazole-1-carboxylate (689260-55-7) → [4-(2,3,5-tri-O-benzyl-β-D-ribofuranosyl)imidazol-1-yl]methyl 2,2-dimethylpropiolate (689260-57-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / aq. NH₄OH / methanol / 3 h / 20 °C

2: 91 percent / NaH / tetrahydrofuran / 5 h / 20 °C

With ammonium hydroxide; sodium hydride; In tetrahydrofuran; methanol;

DOI:10.1016/j.tetlet.2004.01.132

upstream raw materials:

Chloromethyl pivalate

4(5)-2,3,5-tri-O-benzyl-β-D-ribofuranosylimidazole

ethyl 4-(2,3,5-tri-O-benzyl-D-ribofuranosyl)imidazole-1-carboxylate

2,2,2-trichloroethyl 4-(2,3,5-tri-O-benzyl-β-D-ribofuranosyl)imidazole-1-carboxylate

Downstream raw materials:

[4-(5-O-4,4'-dimethoxytrityl-β-D-ribofuranosyl)imidazol-1-yl]methyl 2,2-dimethylpropiolate

2,2-Dimethyl-propionic acid 4-{(2S,3R,4R,5R)-3-allyloxy-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-imidazol-1-ylmethyl ester

4(5)-2,3,5-tri-O-benzyl-β-D-ribofuranosylimidazole

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