pent-4-enyl 2-O-benzoyl-3,5-di-O-benzyl-α-D-arabinofuranoside

Base Information

• Chemical Name: pent-4-enyl 2-O-benzoyl-3,5-di-O-benzyl-α-D-arabinofuranoside
• CAS No.: 765274-05-3
• Molecular Formula: C₃₁H₃₄O₆
• Molecular Weight: 502.607
• Mol file: 765274-05-3.mol

Synonyms:pent-4-enyl 2-O-benzoyl-3,5-di-O-benzyl-α-D-arabinofuranoside

Chemical Property of pent-4-enyl 2-O-benzoyl-3,5-di-O-benzyl-α-D-arabinofuranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of pent-4-enyl 2-O-benzoyl-3,5-di-O-benzyl-α-D-arabinofuranoside

There total 6 articles about pent-4-enyl 2-O-benzoyl-3,5-di-O-benzyl-α-D-arabinofuranoside 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: 91.0%

(2R,3aS,5R,6R,6aS)-6-Benzyloxy-5-benzyloxymethyl-2-pent-4-enyloxy-2-phenyl-tetrahydro-furo[2,3-d][1,3]dioxole → pent-4-enyl 2-O-benzoyl-3,5-di-O-benzyl-α-D-arabinofuranoside (765274-05-3)

Guidance literature:

With tert-butyldiphenylsilyl triflate; In dichloromethane; at 0 ℃;

Reference yield: 91.0%

3,5-di-O-benzyl-β-D-arabinofuranose 1,2-(pent-4-enyl orthobenzoate) (765274-03-1) → pent-4-enyl 2-O-benzoyl-3,5-di-O-benzyl-α-D-arabinofuranoside (765274-05-3)

Guidance literature:

With tert-butyldiphenylsilyl triflate; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1021/ol0490680

Reference yield:

n-Pent-4-enyl alcohol (821-09-0) → pent-4-enyl 2-O-benzoyl-3,5-di-O-benzyl-α-D-arabinofuranoside (765274-05-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 70 percent / 2,6-lutidine; tetra-n-butylammonium iodide / CH₂Cl₂ / 72 h / Heating

2: 75 percent / NaOMe / methanol; CH₂Cl₂ / 2 h / 20 °C

3: 78 percent / NaH / dimethylformamide / 1 h / 0 °C

4: 91 percent / tert-butyldiphenylsilyl triflate / CH₂Cl₂ / 1 h / 0 °C

With 2,6-dimethylpyridine; sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; tert-butyldiphenylsilyl triflate; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ol0490680

upstream raw materials:

3,5-di-O-benzyl-β-D-arabinofuranose 1,2-(pent-4-enyl orthobenzoate)

n-Pent-4-enyl alcohol

β-D-arabinofuranose 1,2-(pent-4-enyl orthobenzoate)

3,5-di-O-benzoyl-β-D-arabinofuranose 1,2-(pent-4-enyl orthobenzoate)

Downstream raw materials:

4-pentenyl 3,5-di-O-benzyl-α-D-arabinofuranoside

4-penten-1-yl 2,3,5-tri-O-benzyl-α-D-arabinofuranoside