(S)-5-Oxo-4-[2-(2-trimethylsilanyl-ethoxycarbonyl)-ethyl]-oxazolidine-3-carboxylic acid benzyl ester

Base Information

• Chemical Name: (S)-5-Oxo-4-[2-(2-trimethylsilanyl-ethoxycarbonyl)-ethyl]-oxazolidine-3-carboxylic acid benzyl ester
• CAS No.: 203919-89-5
• Molecular Formula: C₁₉H₂₇NO₆Si
• Molecular Weight: 393.512
• Mol file: 203919-89-5.mol

Synonyms:(S)-5-Oxo-4-[2-(2-trimethylsilanyl-ethoxycarbonyl)-ethyl]-oxazolidine-3-carboxylic acid benzyl ester

Chemical Property of (S)-5-Oxo-4-[2-(2-trimethylsilanyl-ethoxycarbonyl)-ethyl]-oxazolidine-3-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-5-Oxo-4-[2-(2-trimethylsilanyl-ethoxycarbonyl)-ethyl]-oxazolidine-3-carboxylic acid benzyl ester

There total 1 articles about (S)-5-Oxo-4-[2-(2-trimethylsilanyl-ethoxycarbonyl)-ethyl]-oxazolidine-3-carboxylic 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: 51.0%

2-(Trimethylsilyl)ethanol (2916-68-9) + (S)-3-[3-(benzyloxycarbonyl)-5-oxooxazolidin-4-yl]propanoic acid (23632-67-9) → (S)-5-Oxo-4-[2-(2-trimethylsilanyl-ethoxycarbonyl)-ethyl]-oxazolidine-3-carboxylic acid benzyl ester (203919-89-5)

Guidance literature:

With bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; triethylamine; In dichloromethane; for 10h;

DOI:10.1021/jo972133h

Reference yield:

(S)-5-Oxo-4-[2-(2-trimethylsilanyl-ethoxycarbonyl)-ethyl]-oxazolidine-3-carboxylic acid benzyl ester (203919-89-5) → 2-[4-tert-butoxycarbonyl-4-(4-methylamino-benzoylamino)-butyrylamino]-pentanedioic acid 1-tert-butyl ester 5-(2-trimethylsilanyl-ethyl) ester

Guidance literature:

Multi-step reaction with 6 steps

1: NaOH / tetrahydrofuran

2: H⁺

3: TBAF / tetrahydrofuran

4: EDC; HOBt; DMAP / dimethylformamide

5: H₂ / Pd/C

6: EDC; HOBt; DMAP / dimethylformamide

With dmap; sodium hydroxide; tetrabutyl ammonium fluoride; hydrogen; hydrogen cation; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; palladium on activated charcoal; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1016/S0960-894X(01)00103-2

Reference yield:

(S)-5-Oxo-4-[2-(2-trimethylsilanyl-ethoxycarbonyl)-ethyl]-oxazolidine-3-carboxylic acid benzyl ester (203919-89-5) → (S)-4-[(S)-1-Carboxy-2-(4-hydroxy-3-nitro-phenyl)-ethylcarbamoyl]-2-[(S)-4-carboxy-4-(4-methylamino-benzoylamino)-butyrylamino]-butyric acid (357958-48-6)

Guidance literature:

Multi-step reaction with 9 steps

1: NaOH / tetrahydrofuran

2: H⁺

3: TBAF / tetrahydrofuran

4: EDC; HOBt; DMAP / dimethylformamide

5: H₂ / Pd/C

6: EDC; HOBt; DMAP / dimethylformamide

7: TBAF / tetrahydrofuran

8: EDC; HOBt / dimethylformamide

9: TFA; Et₃SH / CH₂Cl₂

With dmap; sodium hydroxide; tetrabutyl ammonium fluoride; hydrogen; hydrogen cation; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0960-894X(01)00103-2

upstream raw materials:

2-(Trimethylsilyl)ethanol

(S)-3-[3-(benzyloxycarbonyl)-5-oxooxazolidin-4-yl]propanoic acid

Downstream raw materials:

(S)-2-Benzyloxycarbonylamino-pentanedioic acid 1-(3-hydroxy-propyl) ester 5-(2-trimethylsilanyl-ethyl) ester

(S)-2-Benzyloxycarbonylamino-pentanedioic acid 5-(2-trimethylsilanyl-ethyl) ester

(S)-2-(benzyloxycarbonylamino)pentanedioic acid tert-butyl ester

N-Cbz-L-glutamic acid α-tert-butyl ester γ-(2-trimethylsilyl)ethyl ester