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

Base Information

• Chemical Name: 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
• CAS No.: 142545-56-0
• Molecular Formula: C₅₃H₄₉NO₁₅
• Molecular Weight: 939.97
• Mol file: 142545-56-0.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 3 articles about 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 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:

1,3,4,6-tetra-O-benzoyl-2-deoxy-2-phthalimido-β-D-glucopyranose (142545-54-8) → 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 (142545-56-0)

Guidance literature:

Multi-step reaction with 2 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

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

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

Reference yield:

1,3,4,6-tetra-O-benzoyl-2-(2-benzoyloxycarbonylbenzamido)-2-deoxy-β-D-glucopyranose (142545-64-0) → 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 (142545-56-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 91 percent / Ac₂O / pyridine / 25 h / Heating

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

3: 1.) 4 Angstroem mol. sieves, CF₃SO₃Ag, 2.) collidine / 1.) CH₂Cl₂, r.t., 40 min, 2.) CH₂Cl₂, -30 deg C to r.t., 8 h

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

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

Reference yield:

allyl 2-O-acetyl-4-O-benzyl-α-L-rhamnopyranoside (134136-22-4) + 3,4,6-tri-O-benzoyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl bromide (142545-55-9) → 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 (142545-56-0)

Guidance literature:

With 2,3,5-trimethyl-pyridine; 4 A molecular sieve; silver trifluoromethanesulfonate; Yield given. Multistep reaction; 1.) CH₂Cl₂, r.t., 40 min, 2.) CH₂Cl₂, -30 deg C to r.t., 8 h;

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

upstream raw materials:

allyl 2-O-acetyl-4-O-benzyl-α-L-rhamnopyranoside

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

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

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

Downstream raw materials:

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