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-Cbz-L-aspartic acid α-tert-butyl ester

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-Cbz-L-aspartic acid α-tert-butyl ester
• CAS No.: 142699-60-3
• Molecular Formula: C₄₂H₅₈N₄O₂₀
• Molecular Weight: 938.937

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-Cbz-L-aspartic acid α-tert-butyl ester

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-Cbz-L-aspartic acid α-tert-butyl ester

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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-Cbz-L-aspartic acid α-tert-butyl ester

There total 1 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-Cbz-L-aspartic acid α-tert-butyl ester 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: 68.0%

(S)-2-benzyloxycarbonylamino-succinic acid 1-tert-butyl ester (47307-26-6,149967-07-7) + 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) → 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-Cbz-L-aspartic acid α-tert-butyl ester (142699-60-3)

Guidance literature:

With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; triethylamine; In dichloromethane; for 48h; Ambient temperature;

DOI:10.1021/jo00041a015

Reference yield:

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-Cbz-L-aspartic acid α-tert-butyl ester (142699-60-3) → 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-Cbz-L-aspartic acid

Guidance literature:

With trifluoroacetic acid; In dichloromethane; for 0.5h; Ambient temperature;

DOI:10.1021/jo00041a015

Reference yield:

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-Cbz-L-aspartic acid α-tert-butyl ester (142699-60-3) → 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-Cbz-Asn-Leu-Thr-NH2 (142699-61-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 87 mg / CF₃COOH / CH₂Cl₂ / 0.5 h / Ambient temperature

2: 1) NMM, DCC, HOBt / 1) DMF, -10 deg C, 5 min, 2) DMF, r.t., 2 d

With 4-methyl-morpholine; benzotriazol-1-ol; dicyclohexyl-carbodiimide; trifluoroacetic acid; In dichloromethane;

DOI:10.1021/jo00041a015

upstream raw materials:

(S)-2-benzyloxycarbonylamino-succinic acid 1-tert-butyl ester

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

Downstream raw materials:

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-Cbz-Asn-Leu-Thr-NH2

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