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

Base Information

• Chemical Name: 6-phthalimido-1,2,3,4-tetra-O-benzoyl-6-deoxy-β-D-glucopyranose
• CAS No.: 1609983-72-3
• Molecular Formula: C₄₂H₃₃NO₁₂
• Molecular Weight: 743.724
• Mol file: 1609983-72-3.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 2 articles about 6-phthalimido-1,2,3,4-tetra-O-benzoyl-6-deoxy-β-D-glucopyranose 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: 79.0%

phthalic anhydride (85-44-9) + 6-azide-1,2,3,4-tetra-O-benzoyl-6-deoxy-β-D-glucopyranose (1609983-69-8) → 6-phthalimido-1,2,3,4-tetra-O-benzoyl-6-deoxy-β-D-glucopyranose (1609983-72-3)

Guidance literature:

With trimethylphosphane; In tetrahydrofuran; at 20 ℃; for 120h;

DOI:10.1016/j.ejmech.2014.03.080

Reference yield:

1,2,3,4-tetra-O-benzoyl-β-D-glucopyranose (104707-01-9) → 6-phthalimido-1,2,3,4-tetra-O-benzoyl-6-deoxy-β-D-glucopyranose (1609983-72-3)

Guidance literature:

Multi-step reaction with 2 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

With pyridine; dmap; p-toluenesulfonyl chloride; trimethylphosphane; In tetrahydrofuran;

DOI:10.1016/j.ejmech.2014.03.080

Reference yield: 87.0%

6-phthalimido-1,2,3,4-tetra-O-benzoyl-6-deoxy-β-D-glucopyranose (1609983-72-3) + benzyl bromide (100-39-0) → 6-(2'-O-benzyl-phthalimido)-1,2,3,4-tetra-O-benzoyl-6-deoxy-β-D-glucopyranose (1609983-75-6)

Guidance literature:

With potassium carbonate; In tetrahydrofuran; at 60 ℃; for 5h;

DOI:10.1016/j.ejmech.2014.03.080

upstream raw materials:

phthalic anhydride

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

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

Downstream raw materials:

oleanate 28-O-6-phthalimido-6-deoxy-β-D-glucopyranoside

6-(2'-O-benzyl-phthalimido)-2,3,4-tri-O-benzoyl-6-deoxy-α-D-glucopyranoside trichloroacet-imidate

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

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