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

Base Information

• Chemical Name: {4-[(E)-3-(2,3,5-tri-O-benzyl-β-D-ribofuranosyl)prop-1-enyl]imidazolyl}methyl 2,2-dimethylpropionate
• CAS No.: 1346144-34-0
• Molecular Formula: C₃₈H₄₄N₂O₆
• Molecular Weight: 624.777
• Mol file: 1346144-34-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 6 articles about {4-[(E)-3-(2,3,5-tri-O-benzyl-β-D-ribofuranosyl)prop-1-enyl]imidazolyl}methyl 2,2-dimethylpropionate 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: 63.0%

Chloromethyl pivalate (18997-19-8) + 4-[(EZ)-3-(2,3,5-tri-O-benzyl-β-D-ribofuranos-1-yl)prop-1-enyl]-1H-imidazole (1346144-31-7) → {4-[(E)-3-(2,3,5-tri-O-benzyl-β-D-ribofuranosyl)prop-1-enyl]imidazolyl}methyl 2,2-dimethylpropionate (1346144-34-0)

Guidance literature:

4-[(EZ)-3-(2,3,5-tri-O-benzyl-β-D-ribofuranos-1-yl)prop-1-enyl]-1H-imidazole; With sodium hydride; In tetrahydrofuran; mineral oil; at 20 ℃; for 0.5h; Inert atmosphere;

Chloromethyl pivalate; In tetrahydrofuran; mineral oil; at 20 ℃; for 3h; optical yield given as %de; Inert atmosphere;

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-[(E)-3-(2,3,5-tri-O-benzyl-β-D-ribofuranosyl)prop-1-enyl]imidazolyl}methyl 2,2-dimethylpropionate (1346144-34-0)

Guidance literature:

Multi-step reaction with 4 steps

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

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

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

4.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 20 °C / Inert atmosphere

4.2: 3 h / 20 °C / Inert atmosphere

With hydrogenchloride; n-butyllithium; water; sodium hydride; diisobutylaluminium hydride; In tetrahydrofuran; ethanol; hexane; toluene; mineral oil; 2.1: Wittig reaction;

DOI:10.3987/COM-11-12263

Reference yield:

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-[(E)-3-(2,3,5-tri-O-benzyl-β-D-ribofuranosyl)prop-1-enyl]imidazolyl}methyl 2,2-dimethylpropionate (1346144-34-0)

Guidance literature:

Multi-step reaction with 2 steps

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

2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 20 °C / Inert atmosphere

2.2: 3 h / 20 °C / Inert atmosphere

With hydrogenchloride; water; sodium hydride; In tetrahydrofuran; ethanol; mineral oil;

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

Chloromethyl pivalate

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

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

Downstream raw materials:

C₄₁H₄₉N₃O₈

C₅₀H₆₆N₅O₉P