2-tert-butoxycarbonylamino-3-(di-tert-butoxy-phosphoryloxy)-propionic acid benzyl ester

Base Information

• Chemical Name: 2-tert-butoxycarbonylamino-3-(di-tert-butoxy-phosphoryloxy)-propionic acid benzyl ester
• CAS No.: 448959-60-2
• Molecular Formula: C₂₃H₃₈NO₈P
• Molecular Weight: 487.53

Synonyms:2-tert-butoxycarbonylamino-3-(di-tert-butoxy-phosphoryloxy)-propionic acid benzyl ester

Chemical Property of 2-tert-butoxycarbonylamino-3-(di-tert-butoxy-phosphoryloxy)-propionic acid benzyl ester

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Technology Process of 2-tert-butoxycarbonylamino-3-(di-tert-butoxy-phosphoryloxy)-propionic acid benzyl ester

There total 4 articles about 2-tert-butoxycarbonylamino-3-(di-tert-butoxy-phosphoryloxy)-propionic acid benzyl 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: 97.0%

N-tert-butoxycarbonyl-L-serine benzyl ester (59524-02-6) + di-tert-butyl diisopropylphosphoramide (137348-86-8) → 2-tert-butoxycarbonylamino-3-(di-tert-butoxy-phosphoryloxy)-propionic acid benzyl ester (448959-60-2)

Guidance literature:

N-tert-butoxycarbonyl-L-serine benzyl ester; With 1H-tetrazole; In tetrahydrofuran; dichloromethane; for 0.5h;

di-tert-butyl diisopropylphosphoramide; In tetrahydrofuran; dichloromethane; for 15h;

With dihydrogen peroxide; In tetrahydrofuran; dichloromethane; for 3h; Product distribution / selectivity;

Reference yield:

(S)-N-(tert-butoxycarbonyl)serine (3262-72-4) → 2-tert-butoxycarbonylamino-3-(di-tert-butoxy-phosphoryloxy)-propionic acid benzyl ester (448959-60-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / Cs₂CO₃ / dimethylformamide / 12 h / 20 °C

2: tetrazole / tetrahydrofuran; CH₂Cl₂ / 12 h / 20 °C

3: aq. H₂O₂ / 4 h / 20 °C

With 1H-tetrazole; dihydrogen peroxide; caesium carbonate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0960-894X(03)00812-6

Reference yield:

benzyl bromide (100-39-0) → 2-tert-butoxycarbonylamino-3-(di-tert-butoxy-phosphoryloxy)-propionic acid benzyl ester (448959-60-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / Cs₂CO₃ / dimethylformamide / 12 h / 20 °C

2: tetrazole / tetrahydrofuran; CH₂Cl₂ / 12 h / 20 °C

3: aq. H₂O₂ / 4 h / 20 °C

With 1H-tetrazole; dihydrogen peroxide; caesium carbonate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0960-894X(03)00812-6

upstream raw materials:

(S)-N-(tert-butoxycarbonyl)serine

benzyl bromide

N-tert-butoxycarbonyl-L-serine benzyl ester

di-tert-butyl diisopropylphosphoramide

Downstream raw materials:

[2-(di-tert-butoxy-phosphoryloxy)-1-(4-octyl-phenylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester

[2-(di-tert-butoxy-phosphoryloxy)-1-(4-hexyl-phenylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester

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