pent-4-enyl 2,3,4-tri-O-benzyl-6-O-(2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl)-α-D-mannopyranoside

Base Information

• Chemical Name: pent-4-enyl 2,3,4-tri-O-benzyl-6-O-(2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl)-α-D-mannopyranoside
• CAS No.: 1431370-43-2
• Molecular Formula: C₅₈H₅₈O₁₃
• Molecular Weight: 963.091
• Mol file: 1431370-43-2.mol

Synonyms:pent-4-enyl 2,3,4-tri-O-benzyl-6-O-(2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl)-α-D-mannopyranoside

Chemical Property of pent-4-enyl 2,3,4-tri-O-benzyl-6-O-(2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl)-α-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of pent-4-enyl 2,3,4-tri-O-benzyl-6-O-(2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl)-α-D-mannopyranoside

There total 5 articles about pent-4-enyl 2,3,4-tri-O-benzyl-6-O-(2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl)-α-D-mannopyranoside 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: 77.0%

3,5-di-O-benzoyl-β-D-arabinofuranoside-prop-2-ynyl-1,2-orthobenzoate (1431370-34-1) + n-pentenyl 2,3,4-tri-O-benzyl-α-D-mannopyranoside → pent-4-enyl 2,3,4-tri-O-benzyl-6-O-(2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl)-α-D-mannopyranoside (1431370-43-2)

Guidance literature:

With gold(III) chloride; In dichloromethane; at 25 ℃; for 2h; Molecular sieve; Inert atmosphere;

DOI:10.1021/ol400931p

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) → pent-4-enyl 2,3,4-tri-O-benzyl-6-O-(2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl)-α-D-mannopyranoside (1431370-43-2)

Guidance literature:

Multi-step reaction with 5 steps

1: acetyl chloride / 0 - 20 °C / Inert atmosphere

2: pyridine / 0 - 20 °C / Inert atmosphere

3: Acetyl bromide; methanol / dichloromethane / 2 h / 0 °C / Inert atmosphere

4: 2,6-dimethylpyridine; tetra-(n-butyl)ammonium iodide / dichloromethane / 4 h / 20 °C / Inert atmosphere

5: gold(III) chloride / dichloromethane / 2 h / 25 °C / Molecular sieve; Inert atmosphere

With pyridine; 2,6-dimethylpyridine; methanol; gold(III) chloride; Acetyl bromide; tetra-(n-butyl)ammonium iodide; acetyl chloride; In dichloromethane;

DOI:10.1021/ol400931p

Reference yield:

methyl tri-O-benzoyl-α-D-arabinofuranoside (7473-42-9,22861-07-0,38837-17-1,42793-97-5,52783-53-6,52783-87-6,69350-76-1,69927-20-4,84518-41-2,103238-80-8,105309-18-0,109959-28-6,109959-29-7,114923-83-0,120964-98-9) → pent-4-enyl 2,3,4-tri-O-benzyl-6-O-(2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl)-α-D-mannopyranoside (1431370-43-2)

Guidance literature:

Multi-step reaction with 3 steps

1: Acetyl bromide; methanol / dichloromethane / 2 h / 0 °C / Inert atmosphere

2: 2,6-dimethylpyridine; tetra-(n-butyl)ammonium iodide / dichloromethane / 4 h / 20 °C / Inert atmosphere

3: gold(III) chloride / dichloromethane / 2 h / 25 °C / Molecular sieve; Inert atmosphere

With 2,6-dimethylpyridine; methanol; gold(III) chloride; Acetyl bromide; tetra-(n-butyl)ammonium iodide; In dichloromethane;

DOI:10.1021/ol400931p

upstream raw materials:

3,5-di-O-benzoyl-β-D-arabinofuranoside-prop-2-ynyl-1,2-orthobenzoate

D-arabinofuranose

methyl D-arabinofuranoside

methyl tri-O-benzoyl-α-D-arabinofuranoside