allyl 3-O-benzyl-2-deoxy-6-O-p-methoxybenzyl-2-phthalimido-β-D-glucopyranoside

Base Information

• Chemical Name: allyl 3-O-benzyl-2-deoxy-6-O-p-methoxybenzyl-2-phthalimido-β-D-glucopyranoside
• CAS No.: 129354-00-3
• Molecular Formula: C₃₂H₃₃NO₈
• Molecular Weight: 559.616
• Mol file: 129354-00-3.mol

Synonyms:allyl 3-O-benzyl-2-deoxy-6-O-p-methoxybenzyl-2-phthalimido-β-D-glucopyranoside

Chemical Property of allyl 3-O-benzyl-2-deoxy-6-O-p-methoxybenzyl-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-2-deoxy-6-O-p-methoxybenzyl-2-phthalimido-β-D-glucopyranoside

There total 2 articles about allyl 3-O-benzyl-2-deoxy-6-O-p-methoxybenzyl-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:

allyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside (129445-36-9) → allyl 3-O-benzyl-2-deoxy-6-O-p-methoxybenzyl-2-phthalimido-β-D-glucopyranoside (129354-00-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 79 percent / 80percent aq. CH₃COOH / 1.5 h / 80 °C

2: 1.) (Bu₃Sn)2O 2.) Bu₄NBr / 1.) toluene, 2 h, 140 deg C 2.) reflux

With tetrabutylammomium bromide; acetic acid; bis(tri-n-butyltin)oxide;

DOI:10.1016/0008-6215(90)84222-G

Reference yield:

allyl 3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (89067-86-7) + p-methoxybenzyl chloride (824-94-2) → allyl 3-O-benzyl-2-deoxy-6-O-p-methoxybenzyl-2-phthalimido-β-D-glucopyranoside (129354-00-3)

Guidance literature:

With tetrabutylammomium bromide; bis(tri-n-butyltin)oxide; Yield given. Multistep reaction; 1.) toluene, 2 h, 140 deg C 2.) reflux;

DOI:10.1016/0008-6215(90)84222-G

Reference yield: 27.0%

allyl 3-O-benzyl-2-deoxy-6-O-p-methoxybenzyl-2-phthalimido-β-D-glucopyranoside (129354-00-3) + 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl trichloroacetimidate (125946-68-1) → 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 (129354-12-7)

Guidance literature:

With molecular sieve; boron trifluoride diethyl etherate; In dichloromethane; at -70 ℃; for 1.5h;

DOI:10.1016/0008-6215(90)84222-G

upstream raw materials:

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

p-methoxybenzyl chloride

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

Downstream raw materials:

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