allyl (4,6-di-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-2,4-di-O-benzoyl-α-L-fucopyranoside

Base Information

• Chemical Name: allyl (4,6-di-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-2,4-di-O-benzoyl-α-L-fucopyranoside
• CAS No.: 286476-65-1
• Molecular Formula: C₄₁H₄₁NO₁₅
• Molecular Weight: 787.774
• Mol file: 286476-65-1.mol

Synonyms:allyl (4,6-di-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-2,4-di-O-benzoyl-α-L-fucopyranoside

Chemical Property of allyl (4,6-di-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-2,4-di-O-benzoyl-α-L-fucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of allyl (4,6-di-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-2,4-di-O-benzoyl-α-L-fucopyranoside

There total 9 articles about allyl (4,6-di-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-2,4-di-O-benzoyl-α-L-fucopyranoside 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: 97.0%

allyl (4,6-di-O-acetyl-3-O-allyloxycarbonyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-2,4-di-O-benzoyl-α-L-fucopyranoside (286476-64-0) → allyl (4,6-di-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-2,4-di-O-benzoyl-α-L-fucopyranoside (286476-65-1)

Guidance literature:

With morpholine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; Heating;

DOI:10.1016/S0957-4166(99)00585-6

Reference yield:

allyl 2,4-di-O-benzoyl-α-L-fucopyranoside (286476-62-8) → allyl (4,6-di-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-2,4-di-O-benzoyl-α-L-fucopyranoside (286476-65-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 84 percent / trimethylsilyl trifluoromethanesulfonate; 4 Angstroem sieves / CH₂Cl₂ / 0.17 h

2: aq. CF₃CO₂H / CH₂Cl₂ / 0.5 h

3: pyridine / toluene; ethanol; CH₂Cl₂

4: 97 percent / morpholine; tetrakis(triphenylphosphine)palladium / tetrahydrofuran / Heating

With morpholine; pyridine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; trifluoroacetic acid; In tetrahydrofuran; ethanol; dichloromethane; toluene; 1: Condensation / 2: Deprotection / 3: Acetylation / 4: Deprotection;

DOI:10.1016/S0957-4166(99)00585-6

Reference yield:

3-O-allyloxycarbonyl-2-deoxy-4,6-O-isopropylidene-2-phthalimido-β-D-glucopyranosyl trichloroacetimidate (144367-27-1) → allyl (4,6-di-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-2,4-di-O-benzoyl-α-L-fucopyranoside (286476-65-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 84 percent / trimethylsilyl trifluoromethanesulfonate; 4 Angstroem sieves / CH₂Cl₂ / 0.17 h

2: aq. CF₃CO₂H / CH₂Cl₂ / 0.5 h

3: pyridine / toluene; ethanol; CH₂Cl₂

4: 97 percent / morpholine; tetrakis(triphenylphosphine)palladium / tetrahydrofuran / Heating

With morpholine; pyridine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; trifluoroacetic acid; In tetrahydrofuran; ethanol; dichloromethane; toluene; 1: Condensation / 2: Deprotection / 3: Acetylation / 4: Deprotection;

DOI:10.1016/S0957-4166(99)00585-6

upstream raw materials:

allyl (4,6-di-O-acetyl-3-O-allyloxycarbonyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-2,4-di-O-benzoyl-α-L-fucopyranoside

3-O-allyloxycarbonyl-2-deoxy-4,6-O-isopropylidene-2-phthalimido-β-D-glucopyranosyl trichloroacetimidate

allyl 2-O-benzoyl-α-L-fucopyranoside

allyl 2-O-benzoyl-3,4-O-isopropylidene-α-L-fucopyranoside