(S)-2-((S)-2-Benzyloxycarbonylamino-3-phenyl-propionylamino)-N-((2R,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yl)-succinamic acid 2-methoxy-ethyl ester

Base Information

• Chemical Name: (S)-2-((S)-2-Benzyloxycarbonylamino-3-phenyl-propionylamino)-N-((2R,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yl)-succinamic acid 2-methoxy-ethyl ester
• CAS No.: 202266-22-6
• Molecular Formula: C₃₈H₄₈N₄O₁₅
• Molecular Weight: 800.817

Synonyms:(S)-2-((S)-2-Benzyloxycarbonylamino-3-phenyl-propionylamino)-N-((2R,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yl)-succinamic acid 2-methoxy-ethyl ester

Chemical Property of (S)-2-((S)-2-Benzyloxycarbonylamino-3-phenyl-propionylamino)-N-((2R,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yl)-succinamic acid 2-methoxy-ethyl ester

Chemical Property:

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Technology Process of (S)-2-((S)-2-Benzyloxycarbonylamino-3-phenyl-propionylamino)-N-((2R,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yl)-succinamic acid 2-methoxy-ethyl ester

There total 6 articles about (S)-2-((S)-2-Benzyloxycarbonylamino-3-phenyl-propionylamino)-N-((2R,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yl)-succinamic acid 2-methoxy-ethyl 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:

2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranosylamine (4515-24-6) → (S)-2-((S)-2-Benzyloxycarbonylamino-3-phenyl-propionylamino)-N-((2R,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yl)-succinamic acid 2-methoxy-ethyl ester (202266-22-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) isobutyl 2-isobutoxy-1,2-dihydroquinoline-1-carboxylate / 1.) CH₂Cl₂, 15 min, 2.) CH₂Cl₂, 8 h

2: H₂, conc. HCl / 5percent Pd/C / ethanol / 6 h

3: 1.) DCC, 1-hydroxybenzotriazole, 2.) Et₃N / 1.) CH₂Cl₂, 15 min, 2.) CH₂Cl₂, RT, 16 h

With hydrogenchloride; 2-isobutoxy-1-isobutoxycarbonyl-1,2-dihydroquinoline; hydrogen; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In ethanol;

DOI:10.1055/s-1997-1374

Reference yield:

N-benzyloxycarbonyl-L-aspartic acid α-(2-methoxyethyl) ester (202266-07-7) → (S)-2-((S)-2-Benzyloxycarbonylamino-3-phenyl-propionylamino)-N-((2R,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yl)-succinamic acid 2-methoxy-ethyl ester (202266-22-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) isobutyl 2-isobutoxy-1,2-dihydroquinoline-1-carboxylate / 1.) CH₂Cl₂, 15 min, 2.) CH₂Cl₂, 8 h

2: H₂, conc. HCl / 5percent Pd/C / ethanol / 6 h

3: 1.) DCC, 1-hydroxybenzotriazole, 2.) Et₃N / 1.) CH₂Cl₂, 15 min, 2.) CH₂Cl₂, RT, 16 h

With hydrogenchloride; 2-isobutoxy-1-isobutoxycarbonyl-1,2-dihydroquinoline; hydrogen; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In ethanol;

DOI:10.1055/s-1997-1374

Reference yield:

bis(2-methoxyethyl) N-benzyloxycarbonyl-L-aspartate (202266-03-3) → (S)-2-((S)-2-Benzyloxycarbonylamino-3-phenyl-propionylamino)-N-((2R,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yl)-succinamic acid 2-methoxy-ethyl ester (202266-22-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 82 percent / aq. sodium phosphate buffer, lipase A₆ (Amano) / acetone / 1.5 h / 37 °C

2: 1.) isobutyl 2-isobutoxy-1,2-dihydroquinoline-1-carboxylate / 1.) CH₂Cl₂, 15 min, 2.) CH₂Cl₂, 8 h

3: H₂, conc. HCl / 5percent Pd/C / ethanol / 6 h

4: 1.) DCC, 1-hydroxybenzotriazole, 2.) Et₃N / 1.) CH₂Cl₂, 15 min, 2.) CH₂Cl₂, RT, 16 h

With hydrogenchloride; 2-isobutoxy-1-isobutoxycarbonyl-1,2-dihydroquinoline; sodium phosphate buffer; lipase A₆ (Amano); hydrogen; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In ethanol; acetone;

DOI:10.1055/s-1997-1374

upstream raw materials:

N-Cbz-L-Phe

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

N-benzyloxycarbonyl-L-aspartic acid α-(2-methoxyethyl) ester

bis(2-methoxyethyl) N-benzyloxycarbonyl-L-aspartate

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