2-acetamido-1-N-<(N'-benzoylaspartylleucylthreoninamid)-4.1-yl>-2-deoxy-β-D-glucopyranosylamine

Base Information

• Chemical Name: 2-acetamido-1-N-<(N'-benzoylaspartylleucylthreoninamid)-4.1-yl>-2-deoxy-β-D-glucopyranosylamine
• CAS No.: 129835-72-9
• Molecular Formula: C₂₉H₄₄N₆O₁₁
• Molecular Weight: 652.702
• Mol file: 129835-72-9.mol

Synonyms:2-acetamido-1-N-<(N'-benzoylaspartylleucylthreoninamid)-4.1-yl>-2-deoxy-β-D-glucopyranosylamine

Chemical Property of 2-acetamido-1-N-<(N'-benzoylaspartylleucylthreoninamid)-4.1-yl>-2-deoxy-β-D-glucopyranosylamine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-acetamido-1-N-<(N'-benzoylaspartylleucylthreoninamid)-4.1-yl>-2-deoxy-β-D-glucopyranosylamine

There total 7 articles about 2-acetamido-1-N-<(N'-benzoylaspartylleucylthreoninamid)-4.1-yl>-2-deoxy-β-D-glucopyranosylamine 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: 66.0%

C6H5C(O)-Asnβ-(Ac3GlcNAc)LeuThrNH2 (129835-77-4) → 2-acetamido-1-N-<(N'-benzoylaspartylleucylthreoninamid)-4.1-yl>-2-deoxy-β-D-glucopyranosylamine (129835-72-9)

Guidance literature:

With water; triethylamine; In methanol; for 8h; Ambient temperature;

DOI:10.1021/jo00313a013

Reference yield:

2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranosylamine (4515-24-6) → 2-acetamido-1-N-<(N'-benzoylaspartylleucylthreoninamid)-4.1-yl>-2-deoxy-β-D-glucopyranosylamine (129835-72-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 59 percent / 1-hydroxybenzotriazole, dicyclohexylcarbodiimide / tetrahydrofuran / 1) - 10 deg C, 30 min, 2) r.t., 15 h

2: 70 percent / TFA / CH₂Cl₂ / 0.5 h / Ambient temperature

3: 74 percent / 1-hydroxybenzotriazole, dicyclohexylcarbodiimide / tetrahydrofuran / 1) - 10 deg C, 30 min, 2) r.t., 15 h

4: 79 percent / H₂, HOAc, H₂O / Pd-C / methanol / 15 h

5: 74 percent / Et₃N / dioxane / 1) ice-bath, 1 h, 2) r.t., 1 h

6: 66 percent / H₂O, Et₃N / methanol / 8 h / Ambient temperature

With water; hydrogen; benzotriazol-1-ol; acetic acid; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane;

DOI:10.1021/jo00313a013

Reference yield:

2-acetamido-3,4,6-tri-O-acetyl-1-N-[α-(carbobenzyloxy)-β-aspartyl]-2-deoxy-β-D-glucopyranosylamine (38877-33-7) → 2-acetamido-1-N-<(N'-benzoylaspartylleucylthreoninamid)-4.1-yl>-2-deoxy-β-D-glucopyranosylamine (129835-72-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 74 percent / 1-hydroxybenzotriazole, dicyclohexylcarbodiimide / tetrahydrofuran / 1) - 10 deg C, 30 min, 2) r.t., 15 h

2: 79 percent / H₂, HOAc, H₂O / Pd-C / methanol / 15 h

3: 74 percent / Et₃N / dioxane / 1) ice-bath, 1 h, 2) r.t., 1 h

4: 66 percent / H₂O, Et₃N / methanol / 8 h / Ambient temperature

With water; hydrogen; benzotriazol-1-ol; acetic acid; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol;

DOI:10.1021/jo00313a013

upstream raw materials:

C6H5C(O)-Asnβ-(Ac3GlcNAc)LeuThrNH2

2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranosylamine

2-acetamido-3,4,6-tri-O-acetyl-1-N-[α-(carbobenzyloxy)-β-aspartyl]-2-deoxy-β-D-glucopyranosylamine

Z-Asnβ-(Ac3GlcNAc)α-OBu^t