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

Base Information

• Chemical Name: 3,5-di-O-benzoyl-β-D-arabinofuranose 1,2-(pent-4-enyl orthobenzoate)
• CAS No.: 765274-01-9
• Molecular Formula: C₃₁H₃₀O₈
• Molecular Weight: 530.574
• Mol file: 765274-01-9.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 4 articles about 3,5-di-O-benzoyl-β-D-arabinofuranose 1,2-(pent-4-enyl orthobenzoate) 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: 70.0%

n-Pent-4-enyl alcohol (821-09-0) + 2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl bromide (4348-68-9) → 3,5-di-O-benzoyl-β-D-arabinofuranose 1,2-(pent-4-enyl orthobenzoate) (765274-01-9)

Guidance literature:

With 2,6-dimethylpyridine; tetra-(n-butyl)ammonium iodide; In dichloromethane; for 72h; Heating;

DOI:10.1021/ol0490680

Reference yield:

2,3,5-tri-O-benzoyl-α,β-D-arabinofuranosyl bromide (56271-35-3) + n-Pent-4-enyl alcohol (821-09-0) → 3,5-di-O-benzoyl-β-D-arabinofuranose 1,2-(pent-4-enyl orthobenzoate) (765274-01-9)

Guidance literature:

With 2,6-dimethylpyridine; tetra-(n-butyl)ammonium iodide; In dichloromethane; at 20 ℃; for 12h;

DOI:10.1021/jo1021376

Reference yield:

D-arabinofuranose (532-20-7,613-83-2,7261-25-8,7687-39-0,13221-22-2,14795-83-6,15761-67-8,20074-49-1,25545-03-3,25545-04-4,32445-75-3,34436-17-4,36441-93-7,36468-53-8,37110-85-3,37388-49-1,38029-69-5,40461-77-6,40461-89-0,41546-19-4,41546-20-7,41546-21-8,41546-26-3,41546-29-6,41546-30-9,41546-31-0,126872-16-0,131064-98-7) → 3,5-di-O-benzoyl-β-D-arabinofuranose 1,2-(pent-4-enyl orthobenzoate) (765274-01-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: acetyl chloride / 7 h / 20 °C

2.1: pyridine / 12 h / 0 - 20 °C

2.2: 0.75 h / 20 °C

3.1: 2,6-dimethylpyridine; tetra-(n-butyl)ammonium iodide / dichloromethane / 12 h / 20 °C

With pyridine; 2,6-dimethylpyridine; tetra-(n-butyl)ammonium iodide; acetyl chloride; In dichloromethane;

DOI:10.1021/jo1021376

upstream raw materials:

n-Pent-4-enyl alcohol

2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl bromide

2,3,5-tri-O-benzoyl-α,β-D-arabinofuranosyl bromide

D-arabinofuranose

Downstream raw materials:

2,5-di-O-benzoyl-3-O-(2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl)-α-D-arabinofuranosyl fluoride

2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl fluoride

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

(3aS,5R,6R,6aS)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2-pent-4-enyloxy-2-phenyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-ol