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

Base Information

• Chemical Name: <2-(4-Methoxycarbonylbutancarboxamido)ethyl>-2-acetamido-3-O-benzyl-4,6-O-benzyliden-2-desoxy-α-D-galactopyranosid
• CAS No.: 78632-93-6
• Molecular Formula: C₃₁H₄₀N₂O₉
• Molecular Weight: 584.667
• Mol file: 78632-93-6.mol

Synonyms:<2-(4-Methoxycarbonylbutancarboxamido)ethyl>-2-acetamido-3-O-benzyl-4,6-O-benzyliden-2-desoxy-α-D-galactopyranosid

Chemical Property of <2-(4-Methoxycarbonylbutancarboxamido)ethyl>-2-acetamido-3-O-benzyl-4,6-O-benzyliden-2-desoxy-α-D-galactopyranosid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of <2-(4-Methoxycarbonylbutancarboxamido)ethyl>-2-acetamido-3-O-benzyl-4,6-O-benzyliden-2-desoxy-α-D-galactopyranosid

There total 11 articles about <2-(4-Methoxycarbonylbutancarboxamido)ethyl>-2-acetamido-3-O-benzyl-4,6-O-benzyliden-2-desoxy-α-D-galactopyranosid 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%

benzyl bromide (100-39-0) + <2-(4-Methoxycarbonylbutancarboxamido)ethyl>-2-acetamido-4,6-O-benzyliden-2-desoxy-α-D-galactopyranosid (78632-92-5,78632-96-9) → <2-(4-Methoxycarbonylbutancarboxamido)ethyl>-2-acetamido-3-O-benzyl-4,6-O-benzyliden-2-desoxy-α-D-galactopyranosid (78632-93-6)

Guidance literature:

With barium dihydroxide; barium(II) oxide; In N,N-dimethyl-formamide; for 7h; Ambient temperature;

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

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-3-O-benzyl-4,6-O-benzyliden-2-desoxy-α-D-galactopyranosid (78632-93-6)

Guidance literature:

Multi-step reaction with 6 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

With barium dihydroxide; molecular sieve; silver trifluoromethanesulfonate; sodium; acetic acid; dicyclohexyl-carbodiimide; silver carbonate; zinc(II) chloride; barium(II) oxide; zinc; In water; 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-3-O-benzyl-4,6-O-benzyliden-2-desoxy-α-D-galactopyranosid (78632-93-6)

Guidance literature:

Multi-step reaction with 3 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

With barium dihydroxide; sodium; zinc(II) chloride; barium(II) oxide; zinc; In N,N-dimethyl-formamide;

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

upstream raw materials:

5-[2-((4aR,6S,7R,8R,8aR)-7-Acetylamino-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-ethylcarbamoyl]-pentanoic acid methyl ester

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

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

5-[2-((2S,3R,4R,5R,6R)-4,5-Diacetoxy-6-acetoxymethyl-3-azido-tetrahydro-pyran-2-yloxy)-ethylcarbamoyl]-pentanoic acid methyl ester

Downstream raw materials:

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

<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

<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

<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