<2-(4-Methoxycarbonylbutancarboxamido)ethyl>-2-acetamido-6-O-acetyl-3-O-benzyl-2-desoxy-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranosyd

Base Information

• Chemical Name: <2-(4-Methoxycarbonylbutancarboxamido)ethyl>-2-acetamido-6-O-acetyl-3-O-benzyl-2-desoxy-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranosyd
• CAS No.: 78633-01-9
• Molecular Formula: C₄₀H₅₆N₂O₁₉
• Molecular Weight: 868.887
• Mol file: 78633-01-9.mol

Synonyms:

Chemical Property of <2-(4-Methoxycarbonylbutancarboxamido)ethyl>-2-acetamido-6-O-acetyl-3-O-benzyl-2-desoxy-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranosyd

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of <2-(4-Methoxycarbonylbutancarboxamido)ethyl>-2-acetamido-6-O-acetyl-3-O-benzyl-2-desoxy-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranosyd

There total 9 articles about <2-(4-Methoxycarbonylbutancarboxamido)ethyl>-2-acetamido-6-O-acetyl-3-O-benzyl-2-desoxy-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranosyd 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:

3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-galactopyranosyl chloride (67817-37-2) → <2-(4-Methoxycarbonylbutancarboxamido)ethyl>-2-acetamido-6-O-acetyl-3-O-benzyl-2-desoxy-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranosyd (78633-01-9)

Guidance literature:

Multi-step reaction with 8 steps

1: 1) Ag₂CO₃, CF₃SO₃Ag, molecular sieves / 1) CH₂Cl₂, toluene, 2 h; 2) CH₂Cl₂, toluene, 2 d, room temperature

2: 2.41 g / 60percent acetic acid / H₂O / 0.25 h / 80 °C

3: dicyclohexylcarbodiimid / dimethylformamide / 5 h / 0 °C

4: 1) zinc; 2) sodium / 1) acetic acid, room temperature, 30 min; 2) methanol, room temperature, 1 h

5: zinc chloride / neat (no solvent) / 24 h

6: 78 percent / BaO, Ba(OH)2.8H₂O / dimethylformamide / 7 h / Ambient temperature

7: 1.) 60percent acetic acid / 1.) water, 30 min, 80 deg C; 2.) pyridine, dichloromethane, 6 h, room temperature

8: 1) Hg(CN)2, HgBr₂ / 1) MeNO₂, benzene, 55-60 deg C; 2) benzene, 8 h at 60 deg C, then 20 h at room temp.

With barium dihydroxide; molecular sieve; silver trifluoromethanesulfonate; sodium; mercury(II) cyanide; acetic acid; dicyclohexyl-carbodiimide; silver carbonate; mercury dibromide; zinc(II) chloride; barium(II) oxide; zinc; In water; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(00)82583-5

Reference yield:

benzyl bromide (100-39-0) → <2-(4-Methoxycarbonylbutancarboxamido)ethyl>-2-acetamido-6-O-acetyl-3-O-benzyl-2-desoxy-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranosyd (78633-01-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 78 percent / BaO, Ba(OH)2.8H₂O / dimethylformamide / 7 h / Ambient temperature

2: 1.) 60percent acetic acid / 1.) water, 30 min, 80 deg C; 2.) pyridine, dichloromethane, 6 h, room temperature

3: 1) Hg(CN)2, HgBr₂ / 1) MeNO₂, benzene, 55-60 deg C; 2) benzene, 8 h at 60 deg C, then 20 h at room temp.

With barium dihydroxide; mercury(II) cyanide; acetic acid; mercury dibromide; barium(II) oxide; In N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(00)82583-5

Reference yield:

5-[2-((2S,3R,4R,5R,6R)-4,5-Diacetoxy-6-acetoxymethyl-3-azido-tetrahydro-pyran-2-yloxy)-ethylcarbamoyl]-pentanoic acid methyl ester (78632-90-3) → <2-(4-Methoxycarbonylbutancarboxamido)ethyl>-2-acetamido-6-O-acetyl-3-O-benzyl-2-desoxy-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranosyd (78633-01-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 1) zinc; 2) sodium / 1) acetic acid, room temperature, 30 min; 2) methanol, room temperature, 1 h

2: zinc chloride / neat (no solvent) / 24 h

3: 78 percent / BaO, Ba(OH)2.8H₂O / dimethylformamide / 7 h / Ambient temperature

4: 1.) 60percent acetic acid / 1.) water, 30 min, 80 deg C; 2.) pyridine, dichloromethane, 6 h, room temperature

5: 1) Hg(CN)2, HgBr₂ / 1) MeNO₂, benzene, 55-60 deg C; 2) benzene, 8 h at 60 deg C, then 20 h at room temp.

With barium dihydroxide; sodium; mercury(II) cyanide; acetic acid; mercury dibromide; zinc(II) chloride; barium(II) oxide; zinc; In N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(00)82583-5

upstream raw materials:

2<(4-Methoxycarbonylbutancarboxamido)ethyl>-2-acetamido-6-O-benzoyl-3-O-benzyl-2-desoxy-α-D-galactopyranosid

1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside

3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-galactopyranosyl chloride

benzyl bromide

Downstream raw materials:

<2-(4-Methoxycarbonylbutancarboxamido)ethyl>-2-acetamido-3-O-benzyl-2-desoxy-α-D-galactopyranosyd

<2-(4-Methoxycarbonylbutancarboxamido)ethyl>-2-acetamido-6-O-benzoyl-2-desoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranosyd

<2-(4-Methoxycarbonylbutancarboxamido)ethyl>-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1-3)-O-<(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1-4)>-2-acetamido-6-O-benzoyl-2-desoxy-α-D-galactopyranosyd