[(2-{(2-Benzylamino-acetyl)-[((2R,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-ylcarbamoyl)-methyl]-amino}-acetyl)-isobutyl-amino]-acetic acid tert-butyl ester

Base Information

• Chemical Name: [(2-{(2-Benzylamino-acetyl)-[((2R,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-ylcarbamoyl)-methyl]-amino}-acetyl)-isobutyl-amino]-acetic acid tert-butyl ester
• CAS No.: 198225-20-6
• Molecular Formula: C₃₇H₅₅N₅O₁₃
• Molecular Weight: 777.869

Synonyms:[(2-{(2-Benzylamino-acetyl)-[((2R,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-ylcarbamoyl)-methyl]-amino}-acetyl)-isobutyl-amino]-acetic acid tert-butyl ester

Chemical Property of [(2-{(2-Benzylamino-acetyl)-[((2R,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-ylcarbamoyl)-methyl]-amino}-acetyl)-isobutyl-amino]-acetic acid tert-butyl ester

Chemical Property:

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Technology Process of [(2-{(2-Benzylamino-acetyl)-[((2R,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-ylcarbamoyl)-methyl]-amino}-acetyl)-isobutyl-amino]-acetic acid tert-butyl ester

There total 4 articles about [(2-{(2-Benzylamino-acetyl)-[((2R,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-ylcarbamoyl)-methyl]-amino}-acetyl)-isobutyl-amino]-acetic acid 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: 76.0%

benzylamine (100-46-9) + [(2-{(2-Bromo-acetyl)-[((2R,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-ylcarbamoyl)-methyl]-amino}-acetyl)-isobutyl-amino]-acetic acid tert-butyl ester → [(2-{(2-Benzylamino-acetyl)-[((2R,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-ylcarbamoyl)-methyl]-amino}-acetyl)-isobutyl-amino]-acetic acid tert-butyl ester (198225-20-6)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In acetonitrile; for 1h; 0 deg C to r.t.;

DOI:10.1016/S0040-4039(97)10028-4

Reference yield:

N-(2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranosyl)-Nα-(benzyloxycarbonyl)glycineamide (6216-47-3) → [(2-{(2-Benzylamino-acetyl)-[((2R,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-ylcarbamoyl)-methyl]-amino}-acetyl)-isobutyl-amino]-acetic acid tert-butyl ester (198225-20-6)

Guidance literature:

Multi-step reaction with 4 steps

1: H₂ / 10percent Pd-C / methanol / 1 h

2: 70 percent / diisopropylethylamine / acetonitrile / 1 h / 0 °C

3: 90 percent / diisopropylethylamine / CH₂Cl₂ / 0.5 h / 0 °C

4: 76 percent / diisopropylethylamine / acetonitrile / 1 h / 0 deg C to r.t.

With hydrogen; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In methanol; dichloromethane; acetonitrile;

DOI:10.1016/S0040-4039(97)10028-4

Reference yield:

2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-N-glycyl-β-D-glucopyranosylamine (33645-66-8) → [(2-{(2-Benzylamino-acetyl)-[((2R,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-ylcarbamoyl)-methyl]-amino}-acetyl)-isobutyl-amino]-acetic acid tert-butyl ester (198225-20-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 70 percent / diisopropylethylamine / acetonitrile / 1 h / 0 °C

2: 90 percent / diisopropylethylamine / CH₂Cl₂ / 0.5 h / 0 °C

3: 76 percent / diisopropylethylamine / acetonitrile / 1 h / 0 deg C to r.t.

With N-ethyl-N,N-diisopropylamine; In dichloromethane; acetonitrile;

DOI:10.1016/S0040-4039(97)10028-4

upstream raw materials:

benzylamine

N-(2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranosyl)-Nα-(benzyloxycarbonyl)glycineamide

2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-N-glycyl-β-D-glucopyranosylamine

[(2-{[((2R,3R,4R,5S,6R)-4,5-Diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-ylcarbamoyl)-methyl]-amino}-acetyl)-isobutyl-amino]-acetic acid tert-butyl ester

Downstream raw materials:

C₅₃H₈₁N₇O₁₆

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