(4R,5S,8aR)-1-Hydroxy-1-oxo-4-phenyl-octahydro-2-oxa-4a-aza-1λ⁵-phospha-naphthalene-5-carboxylic acid [(S)-2-(1H-indol-3-yl)-1-methylcarbamoyl-ethyl]-amide

Base Information

• Chemical Name: (4R,5S,8aR)-1-Hydroxy-1-oxo-4-phenyl-octahydro-2-oxa-4a-aza-1λ⁵-phospha-naphthalene-5-carboxylic acid [(S)-2-(1H-indol-3-yl)-1-methylcarbamoyl-ethyl]-amide
• CAS No.: 197784-49-9
• Molecular Formula: C₂₆H₃₁N₄O₅P
• Molecular Weight: 510.53

Synonyms:(4R,5S,8aR)-1-Hydroxy-1-oxo-4-phenyl-octahydro-2-oxa-4a-aza-1λ⁵-phospha-naphthalene-5-carboxylic acid [(S)-2-(1H-indol-3-yl)-1-methylcarbamoyl-ethyl]-amide

Chemical Property of (4R,5S,8aR)-1-Hydroxy-1-oxo-4-phenyl-octahydro-2-oxa-4a-aza-1λ⁵-phospha-naphthalene-5-carboxylic acid [(S)-2-(1H-indol-3-yl)-1-methylcarbamoyl-ethyl]-amide

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Technology Process of (4R,5S,8aR)-1-Hydroxy-1-oxo-4-phenyl-octahydro-2-oxa-4a-aza-1λ⁵-phospha-naphthalene-5-carboxylic acid [(S)-2-(1H-indol-3-yl)-1-methylcarbamoyl-ethyl]-amide

There total 6 articles about (4R,5S,8aR)-1-Hydroxy-1-oxo-4-phenyl-octahydro-2-oxa-4a-aza-1λ⁵-phospha-naphthalene-5-carboxylic acid [(S)-2-(1H-indol-3-yl)-1-methylcarbamoyl-ethyl]-amide 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: 81.0%

(4R,5S,8aR)-1-Methoxy-1-oxo-4-phenyl-octahydro-2-oxa-4a-aza-1λ5-phospha-naphthalene-5-carboxylic acid [(S)-2-(1H-indol-3-yl)-1-methylcarbamoyl-ethyl]-amide (197784-47-7) → (4R,5S,8aR)-1-Hydroxy-1-oxo-4-phenyl-octahydro-2-oxa-4a-aza-1λ5-phospha-naphthalene-5-carboxylic acid [(S)-2-(1H-indol-3-yl)-1-methylcarbamoyl-ethyl]-amide (197784-49-9)

Guidance literature:

With trimethylsilyl bromide; In dichloromethane; for 24h; Ambient temperature;

DOI:10.1016/S0960-894X(97)10001-4

Reference yield:

(-)-2-cyano-6-phenyloxazolopiperidine (88056-92-2) → (4R,5S,8aR)-1-Hydroxy-1-oxo-4-phenyl-octahydro-2-oxa-4a-aza-1λ5-phospha-naphthalene-5-carboxylic acid [(S)-2-(1H-indol-3-yl)-1-methylcarbamoyl-ethyl]-amide (197784-49-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 40 percent / HCl, SiO₂ / toluene / 3 h / Ambient temperature

2: SnCl₄ / CH₂Cl₂ / 24 h / Ambient temperature

3: 85 percent / Pd(PPh₃)4, Et₂NH / tetrahydrofuran / 1 h / Ambient temperature

4: 79 percent / EDC, HOBt / CH₂Cl₂ / 48 h / Ambient temperature

5: 81 percent / TMSBr / CH₂Cl₂ / 24 h / Ambient temperature

With hydrogenchloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; trimethylsilyl bromide; silica gel; tin(IV) chloride; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; diethylamine; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1016/S0960-894X(97)10001-4

Reference yield:

(S)-2-amino-3-(1H-indol-3-yl)-N-methylpropanamide (53708-63-7) → (4R,5S,8aR)-1-Hydroxy-1-oxo-4-phenyl-octahydro-2-oxa-4a-aza-1λ5-phospha-naphthalene-5-carboxylic acid [(S)-2-(1H-indol-3-yl)-1-methylcarbamoyl-ethyl]-amide (197784-49-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 79 percent / EDC, HOBt / CH₂Cl₂ / 48 h / Ambient temperature

2: 81 percent / TMSBr / CH₂Cl₂ / 24 h / Ambient temperature

With trimethylsilyl bromide; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In dichloromethane;

DOI:10.1016/S0960-894X(97)10001-4

upstream raw materials:

(4R,5S,8aR)-1-Methoxy-1-oxo-4-phenyl-octahydro-2-oxa-4a-aza-1λ⁵-phospha-naphthalene-5-carboxylic acid [(S)-2-(1H-indol-3-yl)-1-methylcarbamoyl-ethyl]-amide

(-)-2-cyano-6-phenyloxazolopiperidine

(S)-2-amino-3-(1H-indol-3-yl)-N-methylpropanamide

(3R,5S)-3-Phenyl-hexahydro-oxazolo[3,2-a]pyridine-5-carboxylic acid allyl ester

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