N-{2-acetamido-4-O-[3-[[(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)amino]carbonyl]propanoyl]-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl}-3-(benzyloxycarbonylamino)propanoic acid amide

Base Information

• Chemical Name: N-{2-acetamido-4-O-[3-[[(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)amino]carbonyl]propanoyl]-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl}-3-(benzyloxycarbonylamino)propanoic acid amide
• CAS No.: 522634-59-9
• Molecular Formula: C₆₆H₇₅N₅O₁₅
• Molecular Weight: 1178.35
• Mol file: 522634-59-9.mol

Synonyms:N-{2-acetamido-4-O-[3-[[(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)amino]carbonyl]propanoyl]-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl}-3-(benzyloxycarbonylamino)propanoic acid amide

Chemical Property of N-{2-acetamido-4-O-[3-[[(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)amino]carbonyl]propanoyl]-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl}-3-(benzyloxycarbonylamino)propanoic acid amide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-{2-acetamido-4-O-[3-[[(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)amino]carbonyl]propanoyl]-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl}-3-(benzyloxycarbonylamino)propanoic acid amide

There total 9 articles about N-{2-acetamido-4-O-[3-[[(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)amino]carbonyl]propanoyl]-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl}-3-(benzyloxycarbonylamino)propanoic acid amide 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: 58.0%

3-(benzyloxycarbonylamino)propanoic acid (2304-94-1) + 2-acetamido-4-O-[3-[[(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)amino]carbonyl]propanoyl]-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosylamine (522634-54-4) → N-{2-acetamido-4-O-[3-[[(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)amino]carbonyl]propanoyl]-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl}-3-(benzyloxycarbonylamino)propanoic acid amide (522634-59-9)

Guidance literature:

3-(benzyloxycarbonylamino)propanoic acid; With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; In dichloromethane; at 20 ℃; for 6h;

2-acetamido-4-O-[3-[[(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)amino]carbonyl]propanoyl]-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosylamine; In dichloromethane; at 20 ℃;

DOI:10.1081/CAR-120016847

Reference yield:

2-N-acetylamido-2-deoxy-β-D-glucopyranosyl azide (29847-23-2) → N-{2-acetamido-4-O-[3-[[(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)amino]carbonyl]propanoyl]-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl}-3-(benzyloxycarbonylamino)propanoic acid amide (522634-59-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: NaH / dimethylformamide / 0 - 20 °C

1.2: 52 percent / BaO; Ba(OH)2*8H₂O / dimethylformamide; CH₂Cl₂ / Heating

2.1: 100 percent / hydrogen / PtO₂*nH₂O / ethanol / 2.5 h / 20 °C

3.1: 65 percent / molecular sieves (4 Angstroem); EDC; HOBt / NEt₃ / CH₂Cl₂ / 30 h / 20 °C

4.1: 93 percent / hydrogen / Pd/C / methanol / 0.58 h / 20 - 60 °C

5.1: EEDQ / CH₂Cl₂ / 6 h / 20 °C

5.2: 58 percent / CH₂Cl₂ / 20 °C

With 4 A molecular sieve; hydrogen; sodium hydride; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; platinum(IV) oxide; palladium on activated charcoal; triethylamine; In methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1081/CAR-120016847

Reference yield:

benzyl bromide (100-39-0) → N-{2-acetamido-4-O-[3-[[(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)amino]carbonyl]propanoyl]-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl}-3-(benzyloxycarbonylamino)propanoic acid amide (522634-59-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: NaH / dimethylformamide / 0 - 20 °C

1.2: 52 percent / BaO; Ba(OH)2*8H₂O / dimethylformamide; CH₂Cl₂ / Heating

2.1: 100 percent / hydrogen / PtO₂*nH₂O / ethanol / 2.5 h / 20 °C

3.1: 65 percent / molecular sieves (4 Angstroem); EDC; HOBt / NEt₃ / CH₂Cl₂ / 30 h / 20 °C

4.1: 93 percent / hydrogen / Pd/C / methanol / 0.58 h / 20 - 60 °C

5.1: EEDQ / CH₂Cl₂ / 6 h / 20 °C

5.2: 58 percent / CH₂Cl₂ / 20 °C

With 4 A molecular sieve; hydrogen; sodium hydride; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; platinum(IV) oxide; palladium on activated charcoal; triethylamine; In methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1081/CAR-120016847

upstream raw materials:

3-(benzyloxycarbonylamino)propanoic acid

2-acetamido-4-O-[3-[[(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)amino]carbonyl]propanoyl]-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosylamine

2-N-acetylamido-2-deoxy-β-D-glucopyranosyl azide

benzyl bromide

Refernces