N⁴-<2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-3,6-di-O-acetyl-2-deoxy-β-D-glucopyranosyl>-N²-benzoyl-Asn-Leu-Thr-NH2

Base Information

• Chemical Name: N⁴-<2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-3,6-di-O-acetyl-2-deoxy-β-D-glucopyranosyl>-N²-benzoyl-Asn-Leu-Thr-NH2
• CAS No.: 142699-63-6
• Molecular Formula: C₄₇H₆₇N₇O₂₁
• Molecular Weight: 1066.08

Synonyms:N⁴-<2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-3,6-di-O-acetyl-2-deoxy-β-D-glucopyranosyl>-N²-benzoyl-Asn-Leu-Thr-NH2

Chemical Property of N⁴-<2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-3,6-di-O-acetyl-2-deoxy-β-D-glucopyranosyl>-N²-benzoyl-Asn-Leu-Thr-NH2

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Technology Process of N⁴-<2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-3,6-di-O-acetyl-2-deoxy-β-D-glucopyranosyl>-N²-benzoyl-Asn-Leu-Thr-NH2

There total 4 articles about N⁴-<2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-3,6-di-O-acetyl-2-deoxy-β-D-glucopyranosyl>-N²-benzoyl-Asn-Leu-Thr-NH2 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: 79.0%

2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-3,6-di-O-acetyl-2-deoxy-β-D-glucopyranosylamine (29673-51-6) + N-benzoyl-Asp-Leu-Thr-NH2 (142699-65-8) → N4-<2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-3,6-di-O-acetyl-2-deoxy-β-D-glucopyranosyl>-N2-benzoyl-Asn-Leu-Thr-NH2 (142699-63-6)

Guidance literature:

With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; In N,N-dimethyl-formamide; for 6h; Ambient temperature;

DOI:10.1021/jo00041a015

Reference yield:

N-Cbz-Asp(β-OtBu)-Leu-Thr-NH2 (142699-64-7) → N4-<2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-3,6-di-O-acetyl-2-deoxy-β-D-glucopyranosyl>-N2-benzoyl-Asn-Leu-Thr-NH2 (142699-63-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 490 mg / H₂ / Pd/C / methanol / 1241.2 Torr

2: 1) Et₃N / 1) dioxane, r.t., 5 min, 2) dioxane, r.t., 6 h

3: 90 percent / CF₃COOH / CH₂Cl₂ / 0.83 h

4: 79 percent / EEDQ / dimethylformamide / 6 h / Ambient temperature

With hydrogen; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00041a015

Reference yield:

Asp(β-OtBu)-Leu-Thr-NH2 → N4-<2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-3,6-di-O-acetyl-2-deoxy-β-D-glucopyranosyl>-N2-benzoyl-Asn-Leu-Thr-NH2 (142699-63-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 1) Et₃N / 1) dioxane, r.t., 5 min, 2) dioxane, r.t., 6 h

2: 90 percent / CF₃COOH / CH₂Cl₂ / 0.83 h

3: 79 percent / EEDQ / dimethylformamide / 6 h / Ambient temperature

With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; triethylamine; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00041a015

upstream raw materials:

2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-3,6-di-O-acetyl-2-deoxy-β-D-glucopyranosylamine

N-benzoyl-Asp-Leu-Thr-NH₂

N-benzoyl-Asp(β-OtBu)-Leu-Thr-NH2

N-Cbz-Asp(β-OtBu)-Leu-Thr-NH2

Downstream raw materials:

N⁴-<2-acetamido-4-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-2-deoxy-β-D-glucopyranosyl>-N²-benzoyl-Asn-Leu-Thr-NH2

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