(R)-2-[(1-Benzyloxycarbonylamino-ethyl)-methoxy-phosphinoyloxy]-propionic acid methyl ester

Base Information

• Chemical Name: (R)-2-[(1-Benzyloxycarbonylamino-ethyl)-methoxy-phosphinoyloxy]-propionic acid methyl ester
• CAS No.: 289492-02-0
• Molecular Formula: C₁₅H₂₂NO₇P
• Molecular Weight: 359.316
• Mol file: 289492-02-0.mol

Synonyms:(R)-2-[(1-Benzyloxycarbonylamino-ethyl)-methoxy-phosphinoyloxy]-propionic acid methyl ester

Chemical Property of (R)-2-[(1-Benzyloxycarbonylamino-ethyl)-methoxy-phosphinoyloxy]-propionic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-2-[(1-Benzyloxycarbonylamino-ethyl)-methoxy-phosphinoyloxy]-propionic acid methyl ester

There total 5 articles about (R)-2-[(1-Benzyloxycarbonylamino-ethyl)-methoxy-phosphinoyloxy]-propionic acid methyl 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: 53.0%

(R)-Methyl lactate (17392-83-5,2155-30-8) + C11H15ClNO4P (107072-65-1) → (R)-2-[(1-Benzyloxycarbonylamino-ethyl)-methoxy-phosphinoyloxy]-propionic acid methyl ester (289492-02-0)

Guidance literature:

With hydrogenchloride; sodium hydrogencarbonate; triethylamine; In dichloromethane; at 20 ℃; for 120h;

DOI:10.1016/S0960-894X(00)00186-4

Reference yield:

O-benzyl carbamate (621-84-1) → (R)-2-[(1-Benzyloxycarbonylamino-ethyl)-methoxy-phosphinoyloxy]-propionic acid methyl ester (289492-02-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 60 percent / AcOH / 3 h / 20 - 85 °C

2: 72 percent / MeONa; NaOH / 2 h / 20 °C

3: 86 percent / NaOH; aq. HCl / methanol / 12 h / 20 °C

4: SOCl₂ / CH₂Cl₂ / 4 h / 20 °C

5: 53 percent / Et₃N; 1 N aq. HCl; aq. NaHCO₃ / CH₂Cl₂ / 120 h / 20 °C

With hydrogenchloride; sodium hydroxide; thionyl chloride; sodium methylate; sodium hydrogencarbonate; acetic acid; triethylamine; In methanol; dichloromethane; 1: Condensation / 2: transesterification / 3: Hydrolysis / 4: Chlorination / 5: coupling;

DOI:10.1016/S0960-894X(00)00186-4

Reference yield:

N-benzyloxycarbonyl-1-aminoethanephosphonic acid methyl monoester (61989-17-1) → (R)-2-[(1-Benzyloxycarbonylamino-ethyl)-methoxy-phosphinoyloxy]-propionic acid methyl ester (289492-02-0)

Guidance literature:

Multi-step reaction with 2 steps

1: SOCl₂ / CH₂Cl₂ / 4 h / 20 °C

2: 53 percent / Et₃N; 1 N aq. HCl; aq. NaHCO₃ / CH₂Cl₂ / 120 h / 20 °C

With hydrogenchloride; thionyl chloride; sodium hydrogencarbonate; triethylamine; In dichloromethane; 1: Chlorination / 2: coupling;

DOI:10.1016/S0960-894X(00)00186-4

upstream raw materials:

(R)-Methyl lactate

C₁₁H₁₅ClNO₄P

O-benzyl carbamate

N-benzyloxycarbonyl-1-aminoethanephosphonic acid methyl monoester

Downstream raw materials:

(R)-2-[(1-Benzyloxycarbonylamino-ethyl)-hydroxy-phosphinoyloxy]-propionic acid