allyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside

Base Information

• Chemical Name: allyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside
• CAS No.: 129445-36-9
• Molecular Formula: C₃₁H₂₉NO₇
• Molecular Weight: 527.574
• Mol file: 129445-36-9.mol

Synonyms:allyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside

Chemical Property of allyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of allyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside

There total 6 articles about allyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside 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: 48.0%

O-benzyl 2,2,2-trichloroacetimidate (81927-55-1) + allyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside (114853-35-9) → allyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside (129445-36-9)

Guidance literature:

With trifluorormethanesulfonic acid; In dichloromethane; at 0 ℃; for 2h; pH 3;

Reference yield: 25.0%

benzyl bromide (100-39-0) → allyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside (129445-36-9)

Guidance literature:

allyl 2-deoxy-2-acetamido-4,6-O-benzylidene-β-D-glucopyranoside; With potassium hydroxide; ethanol; water;

phthalic anhydride; With triethylamine; In methanol;

benzyl bromide; With sodium hydride; In tetrahydrofuran;

Reference yield:

1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose (10022-13-6) → allyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside (129445-36-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 81 percent / trimethylsilyl triflate / CH₂Cl₂

2: 90 percent / conc. HCl / acetone / 70 °C

3: 95 percent / TsOH / dimethylformamide / 50 °C

4: 48 percent / CF₃SO₃H / CH₂Cl₂ / 2 h / 0 °C / pH 3

With hydrogenchloride; trifluorormethanesulfonic acid; trimethylsilyl trifluoromethanesulfonate; toluene-4-sulfonic acid; In dichloromethane; N,N-dimethyl-formamide; acetone;

upstream raw materials:

O-benzyl 2,2,2-trichloroacetimidate

allyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside

benzyl bromide

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

Downstream raw materials:

allyl 3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

allyl O-(4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-3-O-benzyl-2-deoxy-6-O-p-methoxybenzyl-2-phthalimido-β-D-glucopyranoside

allyl O-(4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-3-O-benzyl-2-deoxy-6-O-p-methoxyphenyl-2-phthalimido-β-D-glucopyranoside

allyl O-(3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-3-O-benzyl-2-deoxy-6-O-p-methoxyphenyl-2-phthalimido-β-D-glucopyranoside