3-{3-tert-butoxycarbonylamino-3-[5-(3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-pentylcarbamoyl]-propionylamino}-N-[5-(3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-pentyl]-succinamic acid benzyl ester

Base Information

• Chemical Name: 3-{3-tert-butoxycarbonylamino-3-[5-(3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-pentylcarbamoyl]-propionylamino}-N-[5-(3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-pentyl]-succinamic acid benzyl ester
• CAS No.: 463313-66-8
• Molecular Formula: C₅₈H₈₄N₄O₂₇
• Molecular Weight: 1269.32

Synonyms:

Chemical Property of 3-{3-tert-butoxycarbonylamino-3-[5-(3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-pentylcarbamoyl]-propionylamino}-N-[5-(3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-pentyl]-succinamic acid benzyl ester

Chemical Property:

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Safty Information:

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Useful:

Technology Process of 3-{3-tert-butoxycarbonylamino-3-[5-(3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-pentylcarbamoyl]-propionylamino}-N-[5-(3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-pentyl]-succinamic acid benzyl ester

There total 9 articles about 3-{3-tert-butoxycarbonylamino-3-[5-(3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-pentylcarbamoyl]-propionylamino}-N-[5-(3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-pentyl]-succinamic acid benzyl 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:

BOC-L-aspartic acid 4-benzyl ester (7536-58-5,98482-77-0) → 3-{3-tert-butoxycarbonylamino-3-[5-(3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-pentylcarbamoyl]-propionylamino}-N-[5-(3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-pentyl]-succinamic acid benzyl ester (463313-66-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 93 percent / DCC / ethyl acetate / 1 h / 0 - 20 °C

2: 95 percent / ethyl acetate / 20 °C

3: H₂ / Pd/C / ethanol; acetic acid / 1 h / 25 °C / 750.06 Torr

4: DCC / ethyl acetate / 1 h / 0 - 20 °C

5: ethyl acetate / 12 h / 25 °C

With hydrogen; dicyclohexyl-carbodiimide; palladium on activated charcoal; In ethanol; acetic acid; ethyl acetate;

DOI:10.1016/S0957-4166(02)00212-4

Reference yield:

5-(benzyloxycarbonylamino)pentyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside (160242-88-6) → 3-{3-tert-butoxycarbonylamino-3-[5-(3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-pentylcarbamoyl]-propionylamino}-N-[5-(3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-pentyl]-succinamic acid benzyl ester (463313-66-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 94 percent / H₂ / Pd/C / ethanol; acetic acid / 1 h / 25 °C / 750.06 Torr

2: 87 percent / ethyl acetate / 20 °C

3: CF₃COOH / CH₂Cl₂ / 1 h / 25 °C

4: ethyl acetate / 12 h / 25 °C

With hydrogen; trifluoroacetic acid; palladium on activated charcoal; In ethanol; dichloromethane; acetic acid; ethyl acetate;

DOI:10.1016/S0957-4166(02)00212-4

Reference yield:

5-<(benzyloxycarbonyl)amino>pentyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (142825-49-8) → 3-{3-tert-butoxycarbonylamino-3-[5-(3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-pentylcarbamoyl]-propionylamino}-N-[5-(3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-pentyl]-succinamic acid benzyl ester (463313-66-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 96 percent / H₂ / Pd/C / ethanol; acetic acid / 1 h / 25 °C / 750.06 Torr

2: 95 percent / ethyl acetate / 20 °C

3: H₂ / Pd/C / ethanol; acetic acid / 1 h / 25 °C / 750.06 Torr

4: DCC / ethyl acetate / 1 h / 0 - 20 °C

5: ethyl acetate / 12 h / 25 °C

With hydrogen; dicyclohexyl-carbodiimide; palladium on activated charcoal; In ethanol; acetic acid; ethyl acetate;

DOI:10.1016/S0957-4166(02)00212-4

upstream raw materials:

(S)-3-tert-Butoxycarbonylamino-N-[5-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-pentyl]-succinamic acid pentafluorophenyl ester

BOC-L-aspartic acid 4-benzyl ester

5-<(benzyloxycarbonyl)amino>pentyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

5-(benzyloxycarbonylamino)pentyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside

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