methyl 2-acetamido-3-O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-6-O-benzyl-2-deoxy-4-O-(4-O-benzyl-2,3-di-O-methyl-α-L-fucopyranosyl)-2-deoxy-β-D-glucopyranoside

Base Information

• Chemical Name: methyl 2-acetamido-3-O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-6-O-benzyl-2-deoxy-4-O-(4-O-benzyl-2,3-di-O-methyl-α-L-fucopyranosyl)-2-deoxy-β-D-glucopyranoside
• CAS No.: 142466-43-1
• Molecular Formula: C₆₀H₇₃NO₁₆
• Molecular Weight: 1064.24
• Mol file: 142466-43-1.mol

Synonyms:methyl 2-acetamido-3-O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-6-O-benzyl-2-deoxy-4-O-(4-O-benzyl-2,3-di-O-methyl-α-L-fucopyranosyl)-2-deoxy-β-D-glucopyranoside

Chemical Property of methyl 2-acetamido-3-O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-6-O-benzyl-2-deoxy-4-O-(4-O-benzyl-2,3-di-O-methyl-α-L-fucopyranosyl)-2-deoxy-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2-acetamido-3-O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-6-O-benzyl-2-deoxy-4-O-(4-O-benzyl-2,3-di-O-methyl-α-L-fucopyranosyl)-2-deoxy-β-D-glucopyranoside

There total 6 articles about methyl 2-acetamido-3-O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-6-O-benzyl-2-deoxy-4-O-(4-O-benzyl-2,3-di-O-methyl-α-L-fucopyranosyl)-2-deoxy-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: 78.0%

(2S,3R,4R,5S)-3-Benzyloxy-6-bromo-4,5-dimethoxy-2-methyl-tetrahydro-pyran (142466-39-5) + methyl 2-acetamido-3-O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-6-O-benzyl-2-deoxy-β-D-glucopyranoside (116981-13-6) → methyl 2-acetamido-3-O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-6-O-benzyl-2-deoxy-4-O-(4-O-benzyl-2,3-di-O-methyl-α-L-fucopyranosyl)-2-deoxy-β-D-glucopyranoside (142466-43-1)

Guidance literature:

With 4 A molecular sieve; tetraethylammonium bromide; In dichloromethane; N,N-dimethyl-formamide; for 48h;

Reference yield:

methyl 2-O-methyl-α-L-fucose (99603-80-2) → methyl 2-acetamido-3-O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-6-O-benzyl-2-deoxy-4-O-(4-O-benzyl-2,3-di-O-methyl-α-L-fucopyranosyl)-2-deoxy-β-D-glucopyranoside (142466-43-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) (n-Bu)2SnO, 2.) (n-Bu)4NF, 4 Angstroem molecular sieves / 1.) C₆H₆, 16 h, reflux, 2.) C₆H₆, r.t., overnight

2: 1.) NaH / 1.) DMF, 0 deg C, 1 h, 2.) 0 deg C to r.t., 16 h

3: 89 percent / acetic acid, 6N HCl / H₂O / 1 h / 65 °C

4: (BrCO)2 / dimethylformamide; CH₂Cl₂ / 0.5 h / Ambient temperature

5: 78 percent / Et₄NBr, 4 Angstroem molecular sieves / dimethylformamide; CH₂Cl₂ / 48 h

With hydrogenchloride; Oxalyl bromide; 4 A molecular sieve; tetraethylammonium bromide; tetrabutyl ammonium fluoride; sodium hydride; di(n-butyl)tin oxide; acetic acid; In dichloromethane; water; N,N-dimethyl-formamide;

Reference yield:

methyl 3,4-O-isopropylidene-2-O-methyl-α-L-fucopyranoside (42822-20-8) → methyl 2-acetamido-3-O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-6-O-benzyl-2-deoxy-4-O-(4-O-benzyl-2,3-di-O-methyl-α-L-fucopyranosyl)-2-deoxy-β-D-glucopyranoside (142466-43-1)

Guidance literature:

Multi-step reaction with 6 steps

1: AcOH / H₂O

2: 1.) (n-Bu)2SnO, 2.) (n-Bu)4NF, 4 Angstroem molecular sieves / 1.) C₆H₆, 16 h, reflux, 2.) C₆H₆, r.t., overnight

3: 1.) NaH / 1.) DMF, 0 deg C, 1 h, 2.) 0 deg C to r.t., 16 h

4: 89 percent / acetic acid, 6N HCl / H₂O / 1 h / 65 °C

5: (BrCO)2 / dimethylformamide; CH₂Cl₂ / 0.5 h / Ambient temperature

6: 78 percent / Et₄NBr, 4 Angstroem molecular sieves / dimethylformamide; CH₂Cl₂ / 48 h

With hydrogenchloride; Oxalyl bromide; 4 A molecular sieve; tetraethylammonium bromide; tetrabutyl ammonium fluoride; sodium hydride; di(n-butyl)tin oxide; acetic acid; In dichloromethane; water; N,N-dimethyl-formamide;

upstream raw materials:

(2S,3R,4R,5S)-3-Benzyloxy-6-bromo-4,5-dimethoxy-2-methyl-tetrahydro-pyran

methyl 2-acetamido-3-O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-6-O-benzyl-2-deoxy-β-D-glucopyranoside

methyl 2-O-methyl-α-L-fucose

methyl 3,4-O-isopropylidene-2-O-methyl-α-L-fucopyranoside

Downstream raw materials:

methyl 2-acetamido-6-O-benzyl-4-O-(4-O-benzyl-2,3-di-O-methyl-α-L-fucopyranosyl)-2-deoxy-3-O-(3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-β-D-glucopyranoside