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

Base Information

• Chemical Name: pent-4-enyl 3,6-di-O-benzyl-2-deoxy-2-tetrachlorophthalimido-β-D-glucopyranoside
• CAS No.: 174356-40-2
• Molecular Formula: C₃₃H₃₁Cl₄NO₇
• Molecular Weight: 695.424
• Mol file: 174356-40-2.mol

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

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

There total 7 articles about pent-4-enyl 3,6-di-O-benzyl-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: 86.0%

pent-4-enyl 4-O-chloroacetyl-3,6-di-O-benzyl-2-deoxy-2-tetrachlorophthalimido-β-D-glucopyranoside → pent-4-enyl 3,6-di-O-benzyl-2-deoxy-2-tetrachlorophthalimido-β-D-glucopyranoside (174356-40-2)

Guidance literature:

With thiourea; In ethanol; ethyl acetate; for 70h;

DOI:10.1021/jo951943v

Reference yield: 78.0%

pent-4-enyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-tetrachlorophthalimido-β-D-glucopyranoside (174356-39-9) → pent-4-enyl 3,6-di-O-benzyl-2-deoxy-2-tetrachlorophthalimido-β-D-glucopyranoside (174356-40-2)

Guidance literature:

With hydrogenchloride; sodium cyanoborohydride; In tetrahydrofuran; diethyl ether; for 0.25h;

DOI:10.1021/jo980427c

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → pent-4-enyl 3,6-di-O-benzyl-2-deoxy-2-tetrachlorophthalimido-β-D-glucopyranoside (174356-40-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 79 percent / p-TsOH / acetonitrile

2: 97 percent / TfOH / CH₂Cl₂; cyclohexane

3: 78 percent / NaBH₃CN, HCl / tetrahydrofuran; diethyl ether / 0.25 h

With hydrogenchloride; trifluorormethanesulfonic acid; sodium cyanoborohydride; toluene-4-sulfonic acid; In tetrahydrofuran; diethyl ether; dichloromethane; cyclohexane; acetonitrile;

DOI:10.1021/jo980427c

upstream raw materials:

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

benzaldehyde dimethyl acetal

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

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

Downstream raw materials:

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

pent-4-enyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1-4)-3,6-di-O-benzyl-2-deoxy-2-tetrachlorophthalimido-β-D-glucopyranoside

octyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1-4)-3,6-di-O-benzyl-2-deoxy-2-tetrachlorophthalimido-β-D-glucopyranoside

hexadecyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1-4)-3,6-di-O-benzyl-2-deoxy-2-tetrachlorophthalimido-β-D-glucopyranoside