methyl 3-O-benzyl-1,2-O-[(1-pent-4-enyloxy)benzylidene]-β-L-threo-hex-4-enopyranuronate

Base Information

• Chemical Name: methyl 3-O-benzyl-1,2-O-[(1-pent-4-enyloxy)benzylidene]-β-L-threo-hex-4-enopyranuronate
• CAS No.: 1447801-86-6
• Molecular Formula: C₂₆H₂₈O₇
• Molecular Weight: 452.504
• Mol file: 1447801-86-6.mol

Synonyms:methyl 3-O-benzyl-1,2-O-[(1-pent-4-enyloxy)benzylidene]-β-L-threo-hex-4-enopyranuronate

Chemical Property of methyl 3-O-benzyl-1,2-O-[(1-pent-4-enyloxy)benzylidene]-β-L-threo-hex-4-enopyranuronate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 3-O-benzyl-1,2-O-[(1-pent-4-enyloxy)benzylidene]-β-L-threo-hex-4-enopyranuronate

There total 4 articles about methyl 3-O-benzyl-1,2-O-[(1-pent-4-enyloxy)benzylidene]-β-L-threo-hex-4-enopyranuronate 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: 90.0%

methyl 4-O-benzoyl-3-O-benzyl-1,2-O-[(1-pent-4-enyloxy)-benzylidene]-β-L-idopyranuronate (1447801-61-7) → methyl 3-O-benzyl-1,2-O-[(1-pent-4-enyloxy)benzylidene]-β-L-threo-hex-4-enopyranuronate (1447801-86-6)

Guidance literature:

With sodium methylate; In methanol;

DOI:10.1021/jo400467g

Reference yield:

methyl 1,2,4-tri-O-benzoyl-3-O-benzyl-β-L-idopyranurate (1447801-85-5) → methyl 3-O-benzyl-1,2-O-[(1-pent-4-enyloxy)benzylidene]-β-L-threo-hex-4-enopyranuronate (1447801-86-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: hydrogen bromide / dichloromethane; acetic acid / 3 h / 0 °C

1.2: 20 h / 20 °C / Inert atmosphere

2.1: sodium methylate / methanol

With hydrogen bromide; sodium methylate; In methanol; dichloromethane; acetic acid;

DOI:10.1021/jo400467g

Reference yield:

methyl 3-O-benzyl-L-idopyranosyluronate (87326-77-0,87326-78-1) → methyl 3-O-benzyl-1,2-O-[(1-pent-4-enyloxy)benzylidene]-β-L-threo-hex-4-enopyranuronate (1447801-86-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: dmap; pyridine / dichloromethane / -40 - 20 °C

2.1: hydrogen bromide / dichloromethane; acetic acid / 3 h / 0 °C

2.2: 20 h / 20 °C / Inert atmosphere

3.1: sodium methylate / methanol

With pyridine; dmap; hydrogen bromide; sodium methylate; In methanol; dichloromethane; acetic acid;

DOI:10.1021/jo400467g

upstream raw materials:

methyl 3-O-benzyl-L-idopyranosyluronate

benzoyl chloride

methyl 1,2,4-tri-O-benzoyl-3-O-benzyl-β-L-idopyranurate

methyl 4-O-benzoyl-3-O-benzyl-1,2-O-[(1-pent-4-enyloxy)-benzylidene]-β-L-idopyranuronate