benzyl 2-acetamido-4-O-(2'-acetamido-4',6'-benzylidene-2'-deoxy-β-D-glucopyranosyl)-2-deoxy-6-O-(2'',3'',4''-tri-O-benzyl-α-L-fucopyranosyl)-β-D-glucopyranoside

Base Information

• Chemical Name: benzyl 2-acetamido-4-O-(2'-acetamido-4',6'-benzylidene-2'-deoxy-β-D-glucopyranosyl)-2-deoxy-6-O-(2'',3'',4''-tri-O-benzyl-α-L-fucopyranosyl)-β-D-glucopyranoside
• CAS No.: 129579-89-1
• Molecular Formula: C₅₇H₆₆N₂O₁₅
• Molecular Weight: 1019.16
• Mol file: 129579-89-1.mol

Synonyms:

Chemical Property of benzyl 2-acetamido-4-O-(2'-acetamido-4',6'-benzylidene-2'-deoxy-β-D-glucopyranosyl)-2-deoxy-6-O-(2'',3'',4''-tri-O-benzyl-α-L-fucopyranosyl)-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl 2-acetamido-4-O-(2'-acetamido-4',6'-benzylidene-2'-deoxy-β-D-glucopyranosyl)-2-deoxy-6-O-(2'',3'',4''-tri-O-benzyl-α-L-fucopyranosyl)-β-D-glucopyranoside

There total 7 articles about benzyl 2-acetamido-4-O-(2'-acetamido-4',6'-benzylidene-2'-deoxy-β-D-glucopyranosyl)-2-deoxy-6-O-(2'',3'',4''-tri-O-benzyl-α-L-fucopyranosyl)-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:

chitobiose octaacetate (117467-63-7) → benzyl 2-acetamido-4-O-(2'-acetamido-4',6'-benzylidene-2'-deoxy-β-D-glucopyranosyl)-2-deoxy-6-O-(2'',3'',4''-tri-O-benzyl-α-L-fucopyranosyl)-β-D-glucopyranoside (129579-89-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 420 mg / HCl / acetic acid; acetic anhydride / 60 h / Ambient temperature

2: Ag₂CO₃ / 48 h / Ambient temperature

3: sodium methoxide / methanol / 4 h / Ambient temperature

4: 73 percent / p-toluenesulfonic acid monohydrate / acetonitrile; dimethylformamide / Ambient temperature

5: 1.) tetraethylammonium bromide, 4 Angstroem molecular sieves / 1.) CH₂Cl₂, DMF, 0.5 h, 2.) CH₂Cl₂, 19 h

With hydrogenchloride; 4 A molecular sieve; tetraethylammonium bromide; sodium methylate; toluene-4-sulfonic acid; silver carbonate; In methanol; acetic anhydride; acetic acid; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1139/v90-148

Reference yield:

benzyl 2-acetylamino-4-O-(2-acetylamino-2-deoxy-β-D-glucopyranosyl)-2-deoxy-β-D-glucopyranoside (19272-52-7) → benzyl 2-acetamido-4-O-(2'-acetamido-4',6'-benzylidene-2'-deoxy-β-D-glucopyranosyl)-2-deoxy-6-O-(2'',3'',4''-tri-O-benzyl-α-L-fucopyranosyl)-β-D-glucopyranoside (129579-89-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 73 percent / p-toluenesulfonic acid monohydrate / acetonitrile; dimethylformamide / Ambient temperature

2: 1.) tetraethylammonium bromide, 4 Angstroem molecular sieves / 1.) CH₂Cl₂, DMF, 0.5 h, 2.) CH₂Cl₂, 19 h

With 4 A molecular sieve; tetraethylammonium bromide; toluene-4-sulfonic acid; In N,N-dimethyl-formamide; acetonitrile;

DOI:10.1139/v90-148

Reference yield:

benzyl 2-acetamido-4-O-(2'-acetamido-2'-deoxy-3',4',6'-tri-O-acetyl-β-D-glucopyranosyl)-2-deoxy-3,6-di-O-acetyl-β-D-glucopyranoside (17188-78-2) → benzyl 2-acetamido-4-O-(2'-acetamido-4',6'-benzylidene-2'-deoxy-β-D-glucopyranosyl)-2-deoxy-6-O-(2'',3'',4''-tri-O-benzyl-α-L-fucopyranosyl)-β-D-glucopyranoside (129579-89-1)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium methoxide / methanol / 4 h / Ambient temperature

2: 73 percent / p-toluenesulfonic acid monohydrate / acetonitrile; dimethylformamide / Ambient temperature

3: 1.) tetraethylammonium bromide, 4 Angstroem molecular sieves / 1.) CH₂Cl₂, DMF, 0.5 h, 2.) CH₂Cl₂, 19 h

With 4 A molecular sieve; tetraethylammonium bromide; sodium methylate; toluene-4-sulfonic acid; In methanol; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1139/v90-148

upstream raw materials:

perbenzyl fucosyl bromide

benzyl 2-acetamido-4-O-(2'-acetamido-4',6'-O-benzylidene-2'-deoxy-β-D-glucopyranosyl)-2-deoxy-β-D-glucopyranoside

benzyl 2-acetylamino-4-O-(2-acetylamino-2-deoxy-β-D-glucopyranosyl)-2-deoxy-β-D-glucopyranoside

benzyl 2-acetamido-4-O-(2'-acetamido-2'-deoxy-3',4',6'-tri-O-acetyl-β-D-glucopyranosyl)-2-deoxy-3,6-di-O-acetyl-β-D-glucopyranoside

Downstream raw materials:

6-O-α-L-fucopyranosyl-di-N-acetylchitobiose