Methyl3-O-benzyl-6-O-(2,3,4-tri-O-benzyl-a-L-fucopyranosyl)-2-deoxy-2-phthalimido-b-D-glucopyranoside

Base Information

• Chemical Name: Methyl3-O-benzyl-6-O-(2,3,4-tri-O-benzyl-a-L-fucopyranosyl)-2-deoxy-2-phthalimido-b-D-glucopyranoside
• CAS No.: 97242-86-9
• Molecular Formula: C₄₉H₅₁NO₁₁
• Molecular Weight: 829.944
• Mol file: 97242-86-9.mol

Synonyms:Methyl3-O-benzyl-6-O-(2,3,4-tri-O-benzyl-a-L-fucopyranosyl)-2-deoxy-2-phthalimido-b-D-glucopyranoside

Chemical Property of Methyl3-O-benzyl-6-O-(2,3,4-tri-O-benzyl-a-L-fucopyranosyl)-2-deoxy-2-phthalimido-b-D-glucopyranoside

Chemical Property:

• PSA: 131.45000
• LogP: 6.42430

Purity/Quality:

95% ^*data from raw suppliers

Methyl3-O-Benzyl-6-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-2-deoxy-2-N-phthalimido-β-D-glucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Methyl 3-O-Benzyl-6-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-2-deoxy-2-N-_x000D_phthalimido-β-D-glucopyranoside (cas# 97242-86-9) is a compound useful in organic synthesis.

Technology Process of Methyl3-O-benzyl-6-O-(2,3,4-tri-O-benzyl-a-L-fucopyranosyl)-2-deoxy-2-phthalimido-b-D-glucopyranoside

There total 6 articles about Methyl3-O-benzyl-6-O-(2,3,4-tri-O-benzyl-a-L-fucopyranosyl)-2-deoxy-2-phthalimido-b-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: 30.0%

perbenzyl fucosyl bromide (33639-77-9) + methyl 3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (97242-85-8) → methyl 3-O-benzyl-2-deoxy-2-phthalimido-6-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-β-D-glucopyranoside (97242-86-9) + methyl 3-O-benzyl-2-deoxy-2-phthalimido-4,6-di-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-β-D-glucopyranoside (97242-87-0)

Guidance literature:

With molecular sieve; tetraethylammonium bromide; In dichloromethane; for 6h; 2.4 equivalents of bromide reagent, rt, overnight;

DOI:10.1139/v85-182

Reference yield:

methyl-2-desoxy-2-phthalimido-β-D-glucopyranoside (76101-14-9) → methyl 3-O-benzyl-2-deoxy-2-phthalimido-6-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-β-D-glucopyranoside (97242-86-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 85 percent / p-toluenesulphonic acid / acetonitrile

2: 86 percent / sodium hydride / 1,2-dimethoxy-ethane

3: 88 percent / 60percent aqueous acetic acid / 0.5 h / 100 °C

4: 42 percent / tetraethylammonium bromide, molecular sieves / CH₂Cl₂ / 6 h / Ambient temperature

With molecular sieve; tetraethylammonium bromide; sodium hydride; toluene-4-sulfonic acid; acetic acid; In 1,2-dimethoxyethane; dichloromethane; acetonitrile;

DOI:10.1139/v85-182

Reference yield:

methyl 4,6-O-benzylidene-2-deoxy-2-phthalimide-β-D-glucopyranoside (81927-56-2) → methyl 3-O-benzyl-2-deoxy-2-phthalimido-6-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-β-D-glucopyranoside (97242-86-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 86 percent / sodium hydride / 1,2-dimethoxy-ethane

2: 88 percent / 60percent aqueous acetic acid / 0.5 h / 100 °C

3: 42 percent / tetraethylammonium bromide, molecular sieves / CH₂Cl₂ / 6 h / Ambient temperature

With molecular sieve; tetraethylammonium bromide; sodium hydride; acetic acid; In 1,2-dimethoxyethane; dichloromethane;

DOI:10.1139/v85-182

upstream raw materials:

perbenzyl fucosyl bromide

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

methyl-2-desoxy-2-phthalimido-β-D-glucopyranoside

methyl 4,6-O-benzylidene-2-deoxy-2-phthalimide-β-D-glucopyranoside

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