(S)-2-[(S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-hydroxy-propionylamino]-hex-5-enoic acid benzyl ester

Base Information

• Chemical Name: (S)-2-[(S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-hydroxy-propionylamino]-hex-5-enoic acid benzyl ester
• CAS No.: 175659-62-8
• Molecular Formula: C₃₁H₃₂N₂O₆
• Molecular Weight: 528.605

Synonyms:(S)-2-[(S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-hydroxy-propionylamino]-hex-5-enoic acid benzyl ester

Chemical Property of (S)-2-[(S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-hydroxy-propionylamino]-hex-5-enoic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-[(S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-hydroxy-propionylamino]-hex-5-enoic acid benzyl ester

There total 1 articles about (S)-2-[(S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-hydroxy-propionylamino]-hex-5-enoic 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: 76.0%

N-(9H-fluoren-9-ylmethoxycarbonyl)-L-serine (73724-45-5) + phenylmethyl (S)-2-amino-5-hexenoate (141362-49-4) → (S)-2-[(S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-hydroxy-propionylamino]-hex-5-enoic acid benzyl ester (175659-62-8)

Guidance literature:

With 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride;

DOI:10.1016/0960-894X(96)00055-8

Reference yield:

(S)-2-[(S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-hydroxy-propionylamino]-hex-5-enoic acid benzyl ester (175659-62-8) → (S)-2-[((3S,6S,8aR)-3-{2-[(S)-2-Benzyloxycarbonylamino-3-(4-hydroxy-phenyl)-propionylamino]-acetylamino}-4-oxo-hexahydro-pyrrolo[2,1-b][1,3]oxazine-6-carbonyl)-amino]-4-methyl-pentanoic acid benzyl ester (175777-26-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) ozone, 2.) triphenylphosphine / 1.) CH₂Cl₂, -78 deg C

2: 1.) trifluoroacetic acid, 2.) trifluoroacetic acid / 1.) CH₂Cl₂, reflux, 1 h, 2.) 3 d

3: 50 percent / trifluoroacetic acid / 72 h

4: 96 percent / H₂ / Pd/C / ethanol

5: 71 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, 1-hydroxybenzotriazole hydrate

6: 79 percent / KF, 18-crown-6 / dimethylformamide / other reagent: piperidine

7: 73 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, 1-hydroxybenzotriazole hydrate

With potassium fluoride; 18-crown-6 ether; hydrogen; ozone; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triphenylphosphine; trifluoroacetic acid; palladium on activated charcoal; In ethanol; N,N-dimethyl-formamide;

DOI:10.1016/0960-894X(96)00055-8

Reference yield:

(S)-2-[(S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-hydroxy-propionylamino]-hex-5-enoic acid benzyl ester (175659-62-8) → (S)-2-[((3S,6S,8aR)-3-Amino-4-oxo-hexahydro-pyrrolo[2,1-b][1,3]oxazine-6-carbonyl)-amino]-4-methyl-pentanoic acid benzyl ester

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) ozone, 2.) triphenylphosphine / 1.) CH₂Cl₂, -78 deg C

2: 1.) trifluoroacetic acid, 2.) trifluoroacetic acid / 1.) CH₂Cl₂, reflux, 1 h, 2.) 3 d

3: 50 percent / trifluoroacetic acid / 72 h

4: 96 percent / H₂ / Pd/C / ethanol

5: 71 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, 1-hydroxybenzotriazole hydrate

6: 79 percent / KF, 18-crown-6 / dimethylformamide / other reagent: piperidine

With potassium fluoride; 18-crown-6 ether; hydrogen; ozone; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triphenylphosphine; trifluoroacetic acid; palladium on activated charcoal; In ethanol; N,N-dimethyl-formamide;

DOI:10.1016/0960-894X(96)00055-8

upstream raw materials:

N-(9H-fluoren-9-ylmethoxycarbonyl)-L-serine

phenylmethyl (S)-2-amino-5-hexenoate

Downstream raw materials:

(S)-2-[((3S,6S,8aR)-3-{2-[(S)-2-Benzyloxycarbonylamino-3-(4-hydroxy-phenyl)-propionylamino]-acetylamino}-4-oxo-hexahydro-pyrrolo[2,1-b][1,3]oxazine-6-carbonyl)-amino]-4-methyl-pentanoic acid benzyl ester

(S)-2-[((3S,6S,8aS)-3-{2-[(S)-2-Benzyloxycarbonylamino-3-(4-hydroxy-phenyl)-propionylamino]-acetylamino}-4-oxo-hexahydro-pyrrolo[2,1-b][1,3]oxazine-6-carbonyl)-amino]-4-methyl-pentanoic acid benzyl ester

(S)-2-[((3S,6S,8aS)-3-Amino-4-oxo-hexahydro-pyrrolo[2,1-b][1,3]oxazine-6-carbonyl)-amino]-4-methyl-pentanoic acid benzyl ester

(3S,6S,8aS)-3-(9H-Fluoren-9-ylmethoxycarbonylamino)-4-oxo-hexahydro-pyrrolo[2,1-b][1,3]oxazine-6-carboxylic acid benzyl ester

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