6-(2'-O-benzyl-phthalimido)-2,3,4-tri-O-benzoyl-6-deoxy-β-D-glucopyranosyl oleanate

Base Information

• Chemical Name: 6-(2'-O-benzyl-phthalimido)-2,3,4-tri-O-benzoyl-6-deoxy-β-D-glucopyranosyl oleanate
• CAS No.: 1609983-87-0
• Molecular Formula: C₇₂H₈₁NO₁₃
• Molecular Weight: 1168.43
• Mol file: 1609983-87-0.mol

Synonyms:6-(2'-O-benzyl-phthalimido)-2,3,4-tri-O-benzoyl-6-deoxy-β-D-glucopyranosyl oleanate

Chemical Property of 6-(2'-O-benzyl-phthalimido)-2,3,4-tri-O-benzoyl-6-deoxy-β-D-glucopyranosyl oleanate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-(2'-O-benzyl-phthalimido)-2,3,4-tri-O-benzoyl-6-deoxy-β-D-glucopyranosyl oleanate

There total 5 articles about 6-(2'-O-benzyl-phthalimido)-2,3,4-tri-O-benzoyl-6-deoxy-β-D-glucopyranosyl oleanate 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%

Oleanolic acid (508-02-1) + 6-(2'-O-benzyl-phthalimido)-2,3,4-tri-O-benzoyl-6-deoxy-α-D-glucopyranosyl bromide (1609983-84-7) → 6-(2'-O-benzyl-phthalimido)-2,3,4-tri-O-benzoyl-6-deoxy-β-D-glucopyranosyl oleanate (1609983-87-0)

Guidance literature:

With tetrabutylammomium bromide; potassium carbonate; In dichloromethane; water; for 6h; Reflux;

DOI:10.1016/j.ejmech.2014.03.080

Reference yield:

1,2,3,4-tetra-O-benzoyl-β-D-glucopyranose (104707-01-9) → 6-(2'-O-benzyl-phthalimido)-2,3,4-tri-O-benzoyl-6-deoxy-β-D-glucopyranosyl oleanate (1609983-87-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: p-toluenesulfonyl chloride; pyridine; dmap / 20 h / 20 °C

1.2: 24 h / 60 °C

2.1: trimethylphosphane / tetrahydrofuran / 120 h / 20 °C

3.1: potassium carbonate / tetrahydrofuran / 5 h / 60 °C

4.1: acetic acid; hydrogen bromide / dichloromethane / 6 h / 20 °C

5.1: potassium carbonate; tetrabutylammomium bromide / dichloromethane; water / 6 h / Reflux

With pyridine; dmap; tetrabutylammomium bromide; hydrogen bromide; potassium carbonate; acetic acid; p-toluenesulfonyl chloride; trimethylphosphane; In tetrahydrofuran; dichloromethane; water;

DOI:10.1016/j.ejmech.2014.03.080

Reference yield:

6-(2'-O-benzyl-phthalimido)-1,2,3,4-tetra-O-benzoyl-6-deoxy-β-D-glucopyranose (1609983-75-6) → 6-(2'-O-benzyl-phthalimido)-2,3,4-tri-O-benzoyl-6-deoxy-β-D-glucopyranosyl oleanate (1609983-87-0)

Guidance literature:

Multi-step reaction with 2 steps

1: acetic acid; hydrogen bromide / dichloromethane / 6 h / 20 °C

2: potassium carbonate; tetrabutylammomium bromide / dichloromethane; water / 6 h / Reflux

With tetrabutylammomium bromide; hydrogen bromide; potassium carbonate; acetic acid; In dichloromethane; water;

DOI:10.1016/j.ejmech.2014.03.080

upstream raw materials:

6-azide-1,2,3,4-tetra-O-benzoyl-6-deoxy-β-D-glucopyranose

1,2,3,4-tetra-O-benzoyl-β-D-glucopyranose

6-phthalimido-1,2,3,4-tetra-O-benzoyl-6-deoxy-β-D-glucopyranose

6-(2'-O-benzyl-phthalimido)-1,2,3,4-tetra-O-benzoyl-6-deoxy-β-D-glucopyranose

Downstream raw materials:

28-O-6-(2'-O-benzyl-phthalimido)-2,3,4-tri-O-benzoyl-6-deoxy-β-D-glucopyranosyl oleanate 3-O-2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside

28-O-6-(2'-O-Benzyl-phthalimido)-2,3,4-tri-O-benzoyl-6-deoxy-β-D-glucopyranosyl oleanate 3-O-2,3,4,6-tetra-O-benzoyl-α-D-mannopyranoside

28-O-6-(2'-O-benzyl-phthalimido)-2,3,4-tri-O-benzoyl-6-deoxy-β-D-glucopyranosyl oleanate 3-O-2,3,4,6-tetra-O-benzoyl-β-D-galactopyranoside

28-O-6-(2'-O-benzyl-phthalimido)-2,3,4-tri-O-benzoyl-6-deoxy-β-D-glucopyranosyl oleanate 3-O-2,3,4,6-tetra-O-benzoyl-β-D-xylopyranoside