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

Base Information

• Chemical Name: (4R,5S,8aR)-1-Methoxy-1-oxo-4-phenyl-octahydro-2-oxa-4a-aza-1λ⁵-phospha-naphthalene-5-carboxylic acid
• CAS No.: 197784-46-6
• Molecular Formula: C₁₅H₂₀NO₅P
• Molecular Weight: 325.301

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

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

Chemical Property:

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

There total 3 articles about (4R,5S,8aR)-1-Methoxy-1-oxo-4-phenyl-octahydro-2-oxa-4a-aza-1λ⁵-phospha-naphthalene-5-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: 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:

(-)-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 (197784-46-6)

Guidance literature:

Multi-step reaction with 3 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

With hydrogenchloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; silica gel; tin(IV) chloride; diethylamine; In tetrahydrofuran; dichloromethane; toluene;

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

Reference yield:

(3R,5S)-3-Phenyl-hexahydro-oxazolo[3,2-a]pyridine-5-carboxylic acid allyl ester (197784-43-3) → (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:

Multi-step reaction with 2 steps

1: SnCl₄ / CH₂Cl₂ / 24 h / Ambient temperature

2: 85 percent / Pd(PPh₃)4, Et₂NH / tetrahydrofuran / 1 h / Ambient temperature

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; tin(IV) chloride; diethylamine; In tetrahydrofuran; 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 allyl ester

(-)-2-cyano-6-phenyloxazolopiperidine

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

Downstream 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

(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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