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

Base Information

Chemical Name:(3S,6S,8aS)-3-(9H-Fluoren-9-ylmethoxycarbonylamino)-4-oxo-hexahydro-pyrrolo[2,1-b][1,3]oxazine-6-carboxylic acid
CAS No.:175659-64-0
Molecular Formula:C₂₃H₂₂N₂O₆
Molecular Weight:422.437
Hs Code.:

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

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

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

There total 1 articles about (3S,6S,8aS)-3-(9H-Fluoren-9-ylmethoxycarbonylamino)-4-oxo-hexahydro-pyrrolo[2,1-b][1,3]oxazine-6-carboxylic acid 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:

: 73724-45-5
N-(9H-fluoren-9-ylmethoxycarbonyl)-L-serine

: 175659-64-0
(3S,6S,8aS)-3-(9H-Fluoren-9-ylmethoxycarbonylamino)-4-oxo-hexahydro-pyrrolo[2,1-b][1,3]oxazine-6-carboxylic acid

Guidance literature:: Multi-step reaction with 4 steps

1: 76 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, 1-hydroxybenzotriazole hydrate

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

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

4: 97 percent / H₂ / Pd/C / ethanol

With hydrogen; ozone; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triphenylphosphine; trifluoroacetic acid; palladium on activated charcoal; In ethanol;
DOI:10.1016/0960-894X(96)00055-8

Reference yield: 86.0%

: 1738-69-8
L-Leucine benzyl ester

: 175659-64-0
(3S,6S,8aS)-3-(9H-Fluoren-9-ylmethoxycarbonylamino)-4-oxo-hexahydro-pyrrolo[2,1-b][1,3]oxazine-6-carboxylic acid

: 175659-65-1
(S)-2-{[(3S,6S,8aS)-3-(9H-Fluoren-9-ylmethoxycarbonylamino)-4-oxo-hexahydro-pyrrolo[2,1-b][1,3]oxazine-6-carbonyl]-amino}-4-methyl-pentanoic acid benzyl ester

Guidance literature:: With 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride;
DOI:10.1016/0960-894X(96)00055-8

Reference yield:

: 175659-64-0
(3S,6S,8aS)-3-(9H-Fluoren-9-ylmethoxycarbonylamino)-4-oxo-hexahydro-pyrrolo[2,1-b][1,3]oxazine-6-carboxylic acid

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

Guidance literature:: Multi-step reaction with 4 steps

1: 86 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, 1-hydroxybenzotriazole hydrate

2: 96 percent / KF, 18-crown-6 / dimethylformamide / other reagent: piperidine

3: 69 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, 1-hydroxybenzotriazole hydrate

4: H₂ / Pd/C / H₂O; tetrahydrofuran

With potassium fluoride; 18-crown-6 ether; hydrogen; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; palladium on activated charcoal; In tetrahydrofuran; water; N,N-dimethyl-formamide;
DOI:10.1016/0960-894X(96)00055-8