<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

Base Information

• Chemical Name: <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
• CAS No.: 78633-06-4
• Molecular Formula: C₅₂H₇₀N₂O₂₈
• Molecular Weight: 1171.12

Synonyms:

Chemical Property of <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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of <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

There total 14 articles about <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 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>-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 (78633-06-4)

Guidance literature:

Multi-step reaction with 12 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.

9: 86 percent / 10percent Pd-C / acetone / 3 h / Ambient temperature

10: 1) Hg(CN)2, HgBr₂ / 1) MeNO₂, room temp., 20 min; 2) MeNO₂, room temp, 3 d

11: 83 percent / CH₂Cl₂; pyridine / 7 h / Ambient temperature

12: 1.) Hg(CN)2, HgBr₂ / 1.) nitromethane, benzene, 4 h; 2.) benzene, 8 h, 80 deg C, after it 20 h, room temperature

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; palladium on activated charcoal; In pyridine; dichloromethane; water; N,N-dimethyl-formamide; acetone;

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

Reference yield:

Acetic acid (2R,3R,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-azido-6-(2-{[1-phenyl-meth-(Z)-ylidene]-amino}-ethoxy)-tetrahydro-pyran-4-yl ester (78632-89-0) → <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 (78633-06-4)

Guidance literature:

Multi-step reaction with 11 steps

1: 2.41 g / 60percent acetic acid / H₂O / 0.25 h / 80 °C

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

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

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

5: 78 percent / BaO, Ba(OH)2.8H₂O / dimethylformamide / 7 h / Ambient temperature

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

7: 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.

8: 86 percent / 10percent Pd-C / acetone / 3 h / Ambient temperature

9: 1) Hg(CN)2, HgBr₂ / 1) MeNO₂, room temp., 20 min; 2) MeNO₂, room temp, 3 d

10: 83 percent / CH₂Cl₂; pyridine / 7 h / Ambient temperature

11: 1.) Hg(CN)2, HgBr₂ / 1.) nitromethane, benzene, 4 h; 2.) benzene, 8 h, 80 deg C, after it 20 h, room temperature

With barium dihydroxide; sodium; mercury(II) cyanide; acetic acid; dicyclohexyl-carbodiimide; mercury dibromide; zinc(II) chloride; barium(II) oxide; zinc; palladium on activated charcoal; In pyridine; dichloromethane; water; N,N-dimethyl-formamide; acetone;

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>-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 (78633-06-4)

Guidance literature:

Multi-step reaction with 9 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.

6: 86 percent / 10percent Pd-C / acetone / 3 h / Ambient temperature

7: 1) Hg(CN)2, HgBr₂ / 1) MeNO₂, room temp., 20 min; 2) MeNO₂, room temp, 3 d

8: 83 percent / CH₂Cl₂; pyridine / 7 h / Ambient temperature

9: 1.) Hg(CN)2, HgBr₂ / 1.) nitromethane, benzene, 4 h; 2.) benzene, 8 h, 80 deg C, after it 20 h, room temperature

With barium dihydroxide; sodium; mercury(II) cyanide; acetic acid; mercury dibromide; zinc(II) chloride; barium(II) oxide; zinc; palladium on activated charcoal; In pyridine; dichloromethane; N,N-dimethyl-formamide; acetone;

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

upstream raw materials:

<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

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

benzoyl cyanide

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

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