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

Base Information

• Chemical Name: 2,2,2-trichloroethyl 4-(2,3,5-tri-O-benzyl-β-D-ribofuranosyl)imidazole-1-carboxylate
• CAS No.: 689260-55-7
• Molecular Formula: C₃₂H₃₁Cl₃N₂O₆
• Molecular Weight: 645.967
• Mol file: 689260-55-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about 2,2,2-trichloroethyl 4-(2,3,5-tri-O-benzyl-β-D-ribofuranosyl)imidazole-1-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: 89.0%

4(5)-2,3,5-tri-O-benzyl-β-D-ribofuranosylimidazole (169139-31-5) + 2,2,2-Trichloroethyl chloroformate (17341-93-4) → 2,2,2-trichloroethyl 4-(2,3,5-tri-O-benzyl-β-D-ribofuranosyl)imidazole-1-carboxylate (689260-55-7)

Guidance literature:

With pyridine; dmap; In benzene; at 20 ℃; for 3h;

DOI:10.1016/j.tet.2005.09.063

Reference yield: 89.0%

2,2,2-trichloroethyl 4-(2,3,5-tri-O-benzyl-β-D-ribofuranosyl)imidazole-1-carboxylate (689260-55-7) → 4(5)-2,3,5-tri-O-benzyl-β-D-ribofuranosylimidazole (169139-31-5)

Guidance literature:

With ammonium hydroxide; In methanol; at 20 ℃; for 3h;

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) → 2,2-Dimethyl-propionic acid 4-((2S,3S,4R,5R)-3,4-bis-benzyloxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-imidazol-1-ylmethyl ester

Guidance literature:

Multi-step reaction with 3 steps

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

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

3: 22 percent / H₂ / Pd/C / ethanol / 16 h / 2206.73 Torr

With ammonium hydroxide; hydrogen; sodium hydride; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol;

DOI:10.1016/j.tetlet.2004.01.132

upstream raw materials:

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

2,2,2-Trichloroethyl chloroformate

Downstream raw materials:

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

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

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