(2R,4S,5R)-2-(2-Naphthylmethyl)-3,4-dimethyl-2-oxo-5-phenyl-1,3,2λ⁵-oxazaphospholidine

Base Information

• Chemical Name: (2R,4S,5R)-2-(2-Naphthylmethyl)-3,4-dimethyl-2-oxo-5-phenyl-1,3,2λ⁵-oxazaphospholidine
• CAS No.: 278605-31-5
• Molecular Formula: C₂₁H₂₂NO₂P
• Molecular Weight: 351.385

Synonyms:(2R,4S,5R)-2-(2-Naphthylmethyl)-3,4-dimethyl-2-oxo-5-phenyl-1,3,2λ⁵-oxazaphospholidine

Chemical Property of (2R,4S,5R)-2-(2-Naphthylmethyl)-3,4-dimethyl-2-oxo-5-phenyl-1,3,2λ⁵-oxazaphospholidine

Chemical Property:

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Technology Process of (2R,4S,5R)-2-(2-Naphthylmethyl)-3,4-dimethyl-2-oxo-5-phenyl-1,3,2λ⁵-oxazaphospholidine

There total 4 articles about (2R,4S,5R)-2-(2-Naphthylmethyl)-3,4-dimethyl-2-oxo-5-phenyl-1,3,2λ⁵-oxazaphospholidine 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: 54.0%

ephedrine (299-42-3,7009-81-6,90-83-5,6912-63-6) + 2-Naphthylmethylphosphonic acid dichloride → (2S,4S,5R)-2-(2-Naphthylmethyl)-3,4-dimethyl-2-oxo-5-phenyl-1,3,2λ5-oxazaphospholidine (278605-34-8) + (2R,4S,5R)-2-(2-Naphthylmethyl)-3,4-dimethyl-2-oxo-5-phenyl-1,3,2λ5-oxazaphospholidine (278605-31-5)

Guidance literature:

With triethylamine; In toluene; at -40 - 20 ℃;

DOI:10.1039/a908086d

Reference yield:

2-Naphthylmethylphosphonic acid (16672-84-7) → (2R,4S,5R)-2-(2-Naphthylmethyl)-3,4-dimethyl-2-oxo-5-phenyl-1,3,2λ5-oxazaphospholidine (278605-31-5)

Guidance literature:

Multi-step reaction with 2 steps

1: (COCl)2; DMF / CH₂Cl₂ / 4 h

2: 24 percent / Et₃N / toluene / -40 - 20 °C

With oxalyl dichloride; triethylamine; N,N-dimethyl-formamide; In dichloromethane; toluene; 1: Substitution / 2: Substitution;

DOI:10.1039/a908086d

Reference yield:

Naphthalen-2-ylmethylphosphonic acid methyl ester → (2R,4S,5R)-2-(2-Naphthylmethyl)-3,4-dimethyl-2-oxo-5-phenyl-1,3,2λ5-oxazaphospholidine (278605-31-5)

Guidance literature:

Multi-step reaction with 4 steps

1: CH₂Cl₂ / 12 h / 20 °C

2: H₂O / CH₂Cl₂ / 0.5 h

3: (COCl)2; DMF / CH₂Cl₂ / 4 h

4: 24 percent / Et₃N / toluene / -40 - 20 °C

With oxalyl dichloride; water; triethylamine; N,N-dimethyl-formamide; In dichloromethane; toluene; 1: Substitution / 2: Hydrolysis / 3: Substitution / 4: Substitution;

DOI:10.1039/a908086d

upstream raw materials:

ephedrine

2-Naphthylmethylphosphonic acid

Downstream raw materials:

(2R,4S,5R)-2-[(1S)-Fluoro(2-naphthyl)methyl]-3,4-dimethyl-2-oxo-5-phenyl-1,3,2λ⁵-oxazaphospholidine

(2R,4S,5R)-2-[(1R)-Fluoro(2-naphthyl)methyl]-3,4-dimethyl-2-oxo-5-phenyl-1,3,2λ⁵-oxazaphospholidine

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