(S)-4-((R)-3-Benzoyloxy-2-methyl-propyl)-5-oxo-oxazolidine-3-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (S)-4-((R)-3-Benzoyloxy-2-methyl-propyl)-5-oxo-oxazolidine-3-carboxylic acid tert-butyl ester
• CAS No.: 753487-53-5
• Molecular Formula: C₁₉H₂₅NO₆
• Molecular Weight: 363.411
• Mol file: 753487-53-5.mol

Synonyms:(S)-4-((R)-3-Benzoyloxy-2-methyl-propyl)-5-oxo-oxazolidine-3-carboxylic acid tert-butyl ester

Chemical Property of (S)-4-((R)-3-Benzoyloxy-2-methyl-propyl)-5-oxo-oxazolidine-3-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-4-((R)-3-Benzoyloxy-2-methyl-propyl)-5-oxo-oxazolidine-3-carboxylic acid tert-butyl ester

There total 1 articles about (S)-4-((R)-3-Benzoyloxy-2-methyl-propyl)-5-oxo-oxazolidine-3-carboxylic acid tert-butyl 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:

formaldehyd (50-00-0,30525-89-4,61233-19-0) + Benzoic acid (2R,4S)-4-tert-butoxycarbonylamino-4-carboxy-2-methyl-butyl ester (753487-52-4) → (S)-4-((R)-3-Benzoyloxy-2-methyl-propyl)-5-oxo-oxazolidine-3-carboxylic acid tert-butyl ester (753487-53-5)

Guidance literature:

With toluene-4-sulfonic acid; In benzene; for 32h;

DOI:10.1021/ol049065n

Reference yield: 100.0%

di-tert-butyl dicarbonate (24424-99-5) + (S)-4-((R)-3-Benzoyloxy-2-methyl-propyl)-5-oxo-oxazolidine-3-carboxylic acid tert-butyl ester (753487-53-5) → Benzoic acid (2R,4S)-4-(tert-butoxycarbonyl-methyl-amino)-4-carboxy-2-methyl-butyl ester (753487-47-7)

Guidance literature:

(S)-4-((R)-3-Benzoyloxy-2-methyl-propyl)-5-oxo-oxazolidine-3-carboxylic acid tert-butyl ester; With triethylsilane; trifluoroacetic acid; at 0 - 20 ℃;

di-tert-butyl dicarbonate; With sodium hydroxide; sodium hydrogencarbonate; In tetrahydrofuran; water;

DOI:10.1021/ol049065n

Reference yield:

(S)-4-((R)-3-Benzoyloxy-2-methyl-propyl)-5-oxo-oxazolidine-3-carboxylic acid tert-butyl ester (753487-53-5) → benzoic acid 4-({3-(tert-butyl-dimethyl-silanyloxy)-3-[1-(1,1-dimethyl-allyl)-1H-indol-3-yl]-2-[2-(9H-fluoren-9-ylmethoxycarbonylamino)-3,5-dimethyl-hex-4-enoylamino]-propionyl}-methyl-amino)-4-(1-carboxy-ethylcarbamoyl)-2-methyl-butyl ester (753487-86-4)

Guidance literature:

Multi-step reaction with 7 steps

1.1: Et₃SiH; TFA / 0 - 20 °C

1.2: 100 percent / NaHCO₃; NaOH / tetrahydrofuran; H₂O

2.1: 79 percent / HOBt; i-Pr₂NEt; EDCI / CH₂Cl₂ / 0 - 20 °C

3.1: TFA / CH₂Cl₂ / 2 h / 20 °C

4.1: 164 mg / i-Pr₂NEt; BOP-Cl / CH₂Cl₂ / 20 °C

5.1: piperidine / CH₂Cl₂ / 2 h / 20 °C

6.1: 163 mg / HOBt; i=Pr₂NEt; EDCI / CH₂Cl₂ / 0 - 20 °C

7.1: N-methylaniline / Pd(PPh₃)4 / tetrahydrofuran / 20 °C

With piperidine; triethylsilane; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; N-methylaniline; trifluoroacetic acid; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ol049065n

upstream raw materials:

formaldehyd

Benzoic acid (2R,4S)-4-tert-butoxycarbonylamino-4-carboxy-2-methyl-butyl ester

Downstream raw materials:

Benzoic acid (2R,4S)-4-(tert-butoxycarbonyl-methyl-amino)-4-carboxy-2-methyl-butyl ester

Benzoic acid (2R,4S)-4-((S)-1-allyloxycarbonyl-ethylcarbamoyl)-2-methyl-4-methylamino-butyl ester

Benzoic acid (2R,4S)-4-((S)-1-allyloxycarbonyl-ethylcarbamoyl)-4-(tert-butoxycarbonyl-methyl-amino)-2-methyl-butyl ester

Benzoic acid (2R,4S)-4-((S)-1-allyloxycarbonyl-ethylcarbamoyl)-4-({(2S,3R)-2-amino-3-(tert-butyl-dimethyl-silanyloxy)-3-[1-(1,1-dimethyl-allyl)-1H-indol-3-yl]-propionyl}-methyl-amino)-2-methyl-butyl ester