4(S)-Benzyl-3-(tert-butoxycarbonyl)-2,2-dimethyl-5(R)-oxazolidineacetic acid

Base Information

• Chemical Name: 4(S)-Benzyl-3-(tert-butoxycarbonyl)-2,2-dimethyl-5(R)-oxazolidineacetic acid
• CAS No.: 158895-85-3
• Molecular Formula: C₁₉H₂₇NO₅
• Molecular Weight: 349.427
• Mol file: 158895-85-3.mol

Synonyms:4(S)-Benzyl-3-(tert-butoxycarbonyl)-2,2-dimethyl-5(R)-oxazolidineacetic acid

Chemical Property of 4(S)-Benzyl-3-(tert-butoxycarbonyl)-2,2-dimethyl-5(R)-oxazolidineacetic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4(S)-Benzyl-3-(tert-butoxycarbonyl)-2,2-dimethyl-5(R)-oxazolidineacetic acid

There total 4 articles about 4(S)-Benzyl-3-(tert-butoxycarbonyl)-2,2-dimethyl-5(R)-oxazolidineacetic acid 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: 100.0%

Ethyl 4(S)-benzyl-3-(tert-butoxycarbonyl)-2,2-dimethyl-5(R)-oxazolidineacetate (158744-40-2) → 4(S)-Benzyl-3-(tert-butoxycarbonyl)-2,2-dimethyl-5(R)-oxazolidineacetic acid (158895-85-3)

Guidance literature:

With sodium hydroxide; In ethanol; for 18h; Ambient temperature;

DOI:10.1021/jo00092a026

Reference yield:

N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) → 4(S)-Benzyl-3-(tert-butoxycarbonyl)-2,2-dimethyl-5(R)-oxazolidineacetic acid (158895-85-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) carbonyldiimidazole

2: NaBH₄ / ethanol / 1 h / -15 - -10 °C

3: 80 percent / TsOH*H₂O / 1.) r.t., 24 h, 2.) 50 deg C, 7 h

4: 100 percent / 1 M aq. NaOH / ethanol / 18 h / Ambient temperature

With sodium hydroxide; sodium tetrahydroborate; toluene-4-sulfonic acid; 1,1'-carbonyldiimidazole; In ethanol;

DOI:10.1021/jo00092a026

Reference yield:

(4S)-40<(tertibutyloxycarbonyl)amino>-3-oxo-5-phenylpentanoic acid ethyl ester (112271-08-6) → 4(S)-Benzyl-3-(tert-butoxycarbonyl)-2,2-dimethyl-5(R)-oxazolidineacetic acid (158895-85-3)

Guidance literature:

Multi-step reaction with 3 steps

1: NaBH₄ / ethanol / 1 h / -15 - -10 °C

2: 80 percent / TsOH*H₂O / 1.) r.t., 24 h, 2.) 50 deg C, 7 h

3: 100 percent / 1 M aq. NaOH / ethanol / 18 h / Ambient temperature

With sodium hydroxide; sodium tetrahydroborate; toluene-4-sulfonic acid; In ethanol;

DOI:10.1021/jo00092a026

upstream raw materials:

Ethyl 4(S)-benzyl-3-(tert-butoxycarbonyl)-2,2-dimethyl-5(R)-oxazolidineacetate

N-tert-butoxycarbonyl-L-phenylalanine

(4S)-40<(tertibutyloxycarbonyl)amino>-3-oxo-5-phenylpentanoic acid ethyl ester

N-(tert-butoxycarbonyl)-4(S)-amino-3(R)-hydroxy-5-phenylpentanoic acid ethyl ester

Downstream raw materials:

2-<3(S)-<amino>-2(R)-hydroxy-4-phenylbutyl>-N-tert-butyldecahydro-(4aS,8aS)-isoquinoline-3(S)-carboxamide

2-[3(S)-[(L-asparaginyl)-amino]-2(R)-hydroxy-4-phenylbutyl]-N-tert-butyl-decahydro(4aS,8aS)-isoquinoline-3(S)-carboxamide

cis-N-butyldecahydro-2-<2(R)-hydroxy-4-phenyl-3(S)-aminobutyl>-(4aS,8aS)-isoquinoline-3(S)-carboxamide

Saquinavir