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

Base Information

• Chemical Name: 6-(2'-O-benzyl-phthalimido)-2,3,4-tri-O-benzoyl-6-deoxy-α-D-glucopyranoside trichloroacet-imidate
• CAS No.: 1609983-78-9
• Molecular Formula: C₄₄H₃₅Cl₃N₂O₁₁
• Molecular Weight: 874.128
• Mol file: 1609983-78-9.mol

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

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

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-α-D-glucopyranoside trichloroacet-imidate

There total 4 articles about 6-(2'-O-benzyl-phthalimido)-2,3,4-tri-O-benzoyl-6-deoxy-α-D-glucopyranoside trichloroacet-imidate 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: 83.0%

6-(2'-O-benzyl-phthalimido)-1,2,3,4-tetra-O-benzoyl-6-deoxy-β-D-glucopyranose (1609983-75-6) + trichloroacetonitrile (545-06-2) → 6-(2'-O-benzyl-phthalimido)-2,3,4-tri-O-benzoyl-6-deoxy-α-D-glucopyranoside trichloroacet-imidate (1609983-78-9)

Guidance literature:

6-(2'-O-benzyl-phthalimido)-1,2,3,4-tetra-O-benzoyl-6-deoxy-β-D-glucopyranose; With hydrazinium monoacetate; In N,N-dimethyl-formamide; at 0 ℃; for 12h;

trichloroacetonitrile; With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 0 - 20 ℃; for 3h;

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-α-D-glucopyranoside trichloroacet-imidate (1609983-78-9)

Guidance literature:

Multi-step reaction with 4 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: hydrazinium monoacetate / N,N-dimethyl-formamide / 12 h / 0 °C

4.2: 3 h / 0 - 20 °C

With pyridine; dmap; hydrazinium monoacetate; potassium carbonate; p-toluenesulfonyl chloride; trimethylphosphane; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1016/j.ejmech.2014.03.080

Reference yield:

6-azide-1,2,3,4-tetra-O-benzoyl-6-deoxy-β-D-glucopyranose (1609983-69-8) → 6-(2'-O-benzyl-phthalimido)-2,3,4-tri-O-benzoyl-6-deoxy-α-D-glucopyranoside trichloroacet-imidate (1609983-78-9)

Guidance literature:

Multi-step reaction with 3 steps

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

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

3.1: hydrazinium monoacetate / N,N-dimethyl-formamide / 12 h / 0 °C

3.2: 3 h / 0 - 20 °C

With hydrazinium monoacetate; potassium carbonate; trimethylphosphane; In tetrahydrofuran; N,N-dimethyl-formamide;

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:

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