4-[(EZ)-3-(2,3,5-tri-O-benzyl-β-D-ribofuranos-1-yl)prop-1-enyl]-1H-imidazole

Base Information

• Chemical Name: 4-[(EZ)-3-(2,3,5-tri-O-benzyl-β-D-ribofuranos-1-yl)prop-1-enyl]-1H-imidazole
• CAS No.: 1346144-31-7
• Molecular Formula: C₃₂H₃₄N₂O₄
• Molecular Weight: 510.633
• Mol file: 1346144-31-7.mol

Synonyms:4-[(EZ)-3-(2,3,5-tri-O-benzyl-β-D-ribofuranos-1-yl)prop-1-enyl]-1H-imidazole

Chemical Property of 4-[(EZ)-3-(2,3,5-tri-O-benzyl-β-D-ribofuranos-1-yl)prop-1-enyl]-1H-imidazole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-[(EZ)-3-(2,3,5-tri-O-benzyl-β-D-ribofuranos-1-yl)prop-1-enyl]-1H-imidazole

There total 5 articles about 4-[(EZ)-3-(2,3,5-tri-O-benzyl-β-D-ribofuranos-1-yl)prop-1-enyl]-1H-imidazole 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: 88.0%

4-[(EZ)-2-(2,3,5-tri-O-benzyl-β-D-ribofuranos-1-yl)prop-1-enyl]-1-trityl-1H-imidazole (1346144-32-8) → 4-[(EZ)-3-(2,3,5-tri-O-benzyl-β-D-ribofuranos-1-yl)prop-1-enyl]-1H-imidazole (1346144-31-7)

Guidance literature:

With hydrogenchloride; water; In ethanol; for 2.5h; Inert atmosphere; Reflux;

DOI:10.3987/COM-11-12263

Reference yield:

methyl 3,6-anhydro-4,5,7-tri-O-benzyl-2-deoxy-β-D-alloheptonate (56703-51-6) → 4-[(EZ)-3-(2,3,5-tri-O-benzyl-β-D-ribofuranos-1-yl)prop-1-enyl]-1H-imidazole (1346144-31-7)

Guidance literature:

Multi-step reaction with 3 steps

1: diisobutylaluminium hydride / toluene / 0.58 h / -70 °C / Inert atmosphere

2: n-butyllithium / tetrahydrofuran; hexane / -70 - 20 °C / Inert atmosphere

3: hydrogenchloride; water / ethanol / 2.5 h / Inert atmosphere; Reflux

With hydrogenchloride; n-butyllithium; water; diisobutylaluminium hydride; In tetrahydrofuran; ethanol; hexane; toluene; 2: Wittig reaction;

DOI:10.3987/COM-11-12263

Reference yield:

2-(2,3,5-tri-O-benzyl-β-D-ribofuranosyl)acetaldehyde (1346144-27-1) → 4-[(EZ)-3-(2,3,5-tri-O-benzyl-β-D-ribofuranos-1-yl)prop-1-enyl]-1H-imidazole (1346144-31-7)

Guidance literature:

Multi-step reaction with 2 steps

1: n-butyllithium / tetrahydrofuran; hexane / -70 - 20 °C / Inert atmosphere

2: hydrogenchloride; water / ethanol / 2.5 h / Inert atmosphere; Reflux

With hydrogenchloride; n-butyllithium; water; In tetrahydrofuran; ethanol; hexane; 1: Wittig reaction;

DOI:10.3987/COM-11-12263

upstream raw materials:

4-[(EZ)-2-(2,3,5-tri-O-benzyl-β-D-ribofuranos-1-yl)prop-1-enyl]-1-trityl-1H-imidazole

methyl 3,6-anhydro-4,5,7-tri-O-benzyl-2-deoxy-β-D-alloheptonate

2-(2,3,5-tri-O-benzyl-β-D-ribofuranosyl)acetaldehyde

(Z)-(4S,5R,6R)-4,5,7-Tris-benzyloxy-6-hydroxy-hept-2-enoic acid methyl ester

Downstream raw materials:

C₄₁H₄₉N₃O₈

C₅₀H₆₆N₅O₉P

{4-[(E)-3-(2,3,5-tri-O-benzyl-β-D-ribofuranosyl)prop-1-enyl]imidazolyl}methyl 2,2-dimethylpropionate