(4R,5S,8aR)-1-Methoxy-1-oxo-4-phenyl-octahydro-2-oxa-4a-aza-1λ⁵-phospha-naphthalene-5-carboxylic acid allyl ester

Base Information

• Chemical Name: (4R,5S,8aR)-1-Methoxy-1-oxo-4-phenyl-octahydro-2-oxa-4a-aza-1λ⁵-phospha-naphthalene-5-carboxylic acid allyl ester
• CAS No.: 197784-45-5
• Molecular Formula: C₁₈H₂₄NO₅P
• Molecular Weight: 365.366

Synonyms:(4R,5S,8aR)-1-Methoxy-1-oxo-4-phenyl-octahydro-2-oxa-4a-aza-1λ⁵-phospha-naphthalene-5-carboxylic acid allyl ester

Chemical Property of (4R,5S,8aR)-1-Methoxy-1-oxo-4-phenyl-octahydro-2-oxa-4a-aza-1λ⁵-phospha-naphthalene-5-carboxylic acid allyl ester

Chemical Property:

Purity/Quality:

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MSDS Files:

Useful:

Technology Process of (4R,5S,8aR)-1-Methoxy-1-oxo-4-phenyl-octahydro-2-oxa-4a-aza-1λ⁵-phospha-naphthalene-5-carboxylic acid allyl ester

There total 1 articles about (4R,5S,8aR)-1-Methoxy-1-oxo-4-phenyl-octahydro-2-oxa-4a-aza-1λ⁵-phospha-naphthalene-5-carboxylic acid allyl 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-cyano-6-phenyloxazolopiperidine (88056-92-2) → (4R,5S,8aR)-1-Methoxy-1-oxo-4-phenyl-octahydro-2-oxa-4a-aza-1λ5-phospha-naphthalene-5-carboxylic acid allyl ester (197784-45-5)

Guidance literature:

Multi-step reaction with 2 steps

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

2: SnCl₄ / CH₂Cl₂ / 24 h / Ambient temperature

With hydrogenchloride; silica gel; tin(IV) chloride; In dichloromethane; toluene;

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

Reference yield: 85.0%

(4R,5S,8aR)-1-Methoxy-1-oxo-4-phenyl-octahydro-2-oxa-4a-aza-1λ5-phospha-naphthalene-5-carboxylic acid allyl ester (197784-45-5) → (4R,5S,8aR)-1-Methoxy-1-oxo-4-phenyl-octahydro-2-oxa-4a-aza-1λ5-phospha-naphthalene-5-carboxylic acid (197784-46-6)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; diethylamine; In tetrahydrofuran; for 1h; Ambient temperature;

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

Reference yield:

(4R,5S,8aR)-1-Methoxy-1-oxo-4-phenyl-octahydro-2-oxa-4a-aza-1λ5-phospha-naphthalene-5-carboxylic acid allyl ester (197784-45-5) → {(2R,6S)-6-[(S)-2-(1H-Indol-3-yl)-1-methylcarbamoyl-ethylcarbamoyl]-piperidin-2-yl}-phosphonic acid monophenethyl ester

Guidance literature:

Multi-step reaction with 4 steps

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

2: 79 percent / EDC, HOBt / CH₂Cl₂ / 48 h / Ambient temperature

3: 81 percent / TMSBr / CH₂Cl₂ / 24 h / Ambient temperature

4: 33 percent / H₂ / Pd(OH)2/C / methanol / 20 h / 3375.3 Torr / Ambient temperature

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; trimethylsilyl bromide; hydrogen; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; diethylamine; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane;

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

upstream raw materials:

(-)-2-cyano-6-phenyloxazolopiperidine

Downstream raw materials:

(4R,5S,8aR)-1-Methoxy-1-oxo-4-phenyl-octahydro-2-oxa-4a-aza-1λ⁵-phospha-naphthalene-5-carboxylic acid

(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

(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

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