pent-4-enyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-tetrachlorophthalimido-β-D-glucopyranoside

Base Information

• Chemical Name: pent-4-enyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-tetrachlorophthalimido-β-D-glucopyranoside
• CAS No.: 174356-39-9
• Molecular Formula: C₃₃H₂₉Cl₄NO₇
• Molecular Weight: 693.408
• Mol file: 174356-39-9.mol

Synonyms:pent-4-enyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-tetrachlorophthalimido-β-D-glucopyranoside

Chemical Property of pent-4-enyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-tetrachlorophthalimido-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of pent-4-enyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-tetrachlorophthalimido-β-D-glucopyranoside

There total 6 articles about pent-4-enyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-tetrachlorophthalimido-β-D-glucopyranoside 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: 97.0%

O-benzyl 2,2,2-trichloroacetimidate (81927-55-1) + pent-4-enyl 4,6-O-benzylidene-2-tetrachlorophthalimido-2-deoxy-β-D-glucopyranoside (174356-32-2) → pent-4-enyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-tetrachlorophthalimido-β-D-glucopyranoside (174356-39-9)

Guidance literature:

With trifluorormethanesulfonic acid; In dichloromethane; cyclohexane; for 10h;

DOI:10.1016/S0968-0896(96)00173-3

Reference yield:

pent-4-enyl 2-deoxy-2-tetrachlorophthalimido-β-D-glucopyranoside (182002-91-1) → pent-4-enyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-tetrachlorophthalimido-β-D-glucopyranoside (174356-39-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 79 percent / p-TsOH / acetonitrile

2: 97 percent / TfOH / CH₂Cl₂; cyclohexane

With trifluorormethanesulfonic acid; toluene-4-sulfonic acid; In dichloromethane; cyclohexane; acetonitrile;

DOI:10.1021/jo980427c

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → pent-4-enyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-tetrachlorophthalimido-β-D-glucopyranoside (174356-39-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 79 percent / p-TsOH / acetonitrile

2: 97 percent / TfOH / CH₂Cl₂; cyclohexane

With trifluorormethanesulfonic acid; toluene-4-sulfonic acid; In dichloromethane; cyclohexane; acetonitrile;

DOI:10.1021/jo980427c

upstream raw materials:

O-benzyl 2,2,2-trichloroacetimidate

pent-4-enyl 4,6-O-benzylidene-2-tetrachlorophthalimido-2-deoxy-β-D-glucopyranoside

benzaldehyde dimethyl acetal

pent-4-enyl 2-deoxy-2-tetrachlorophthalimido-β-D-glucopyranoside

Downstream raw materials:

pent-4-enyl 3,6-di-O-benzyl-2-deoxy-2-tetrachlorophthalimido-β-D-glucopyranoside

pent-4-enyl 2-azido-2-deoxy-3-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside

hexadecyl 3,6-di-O-benzyl-2-tetrachlorophthalimido-2-deoxy-β-D-glucopyranoside