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

Base Information

• Chemical Name: 1,3,4,6-tetra-O-benzoyl-2-deoxy-2-phthalimido-β-D-glucopyranose
• CAS No.: 142545-54-8
• Molecular Formula: C₄₂H₃₁NO₁₁
• Molecular Weight: 725.708
• Mol file: 142545-54-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about 1,3,4,6-tetra-O-benzoyl-2-deoxy-2-phthalimido-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: 91.0%

1,3,4,6-tetra-O-benzoyl-2-(2-benzoyloxycarbonylbenzamido)-2-deoxy-β-D-glucopyranose (142545-64-0) → 1,3,4,6-tetra-O-benzoyl-2-deoxy-2-phthalimido-β-D-glucopyranose (142545-54-8)

Guidance literature:

With acetic anhydride; In pyridine; for 25h; Heating;

DOI:10.1016/0008-6215(92)84133-D

Reference yield:

1,3,4,6-tetra-O-benzoyl-2-deoxy-2-phthalimido-β-D-glucopyranose (142545-54-8) → 3,4,6-tri-O-benzoyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl bromide (142545-55-9)

Guidance literature:

With hydrogen bromide; acetic acid; In dichloromethane; for 2h; Yield given; Ambient temperature;

DOI:10.1016/0008-6215(92)84133-D

Reference yield:

1,3,4,6-tetra-O-benzoyl-2-deoxy-2-phthalimido-β-D-glucopyranose (142545-54-8) → allyl 2-O-(2-O-benzoyl-4-O-benzyl-3-O-<<2-(trimethylsilyl)ethoxy>methyl>-α-L-rhamnopyranosyl)-3-O-(3,4,6-tri-O-benzoyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-4-O-benzyl-α-L-rhamnopyranoside

Guidance literature:

Multi-step reaction with 4 steps

1: 48percent HBr, HOAc / CH₂Cl₂ / 2 h / Ambient temperature

2: 1.) 4 Angstroem mol. sieves, CF₃SO₃Ag, 2.) collidine / 1.) CH₂Cl₂, r.t., 40 min, 2.) CH₂Cl₂, -30 deg C to r.t., 8 h

3: 76 percent / methanolic HCl / CH₂Cl₂ / 72 h / Ambient temperature

4: 61 percent / silver trifluoromethanesulfonate, 1,1,3,3-tetramethylurea / CH₂Cl₂ / 17 h / -78 deg C to r.t.

With 2,3,5-trimethyl-pyridine; hydrogenchloride; 4 A molecular sieve; hydrogen bromide; silver trifluoromethanesulfonate; acetic acid; tetramethylurea; In dichloromethane;

DOI:10.1016/0008-6215(92)84133-D

upstream raw materials:

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

Downstream raw materials:

3,4,6-tri-O-benzoyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl bromide

allyl 3-O-(3,4,6-tri-O-benzoyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-4-O-benzyl-α-L-rhamnopyranoside

allyl 3-O-(3,4,6-tri-O-benzoyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-2-O-acetyl-4-O-benzyl-α-L-rhamnopyranoside