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

Base Information

• Chemical Name: Ethyl 4(S)-benzyl-3-(tert-butoxycarbonyl)-2,2-dimethyl-5(R)-oxazolidineacetate
• CAS No.: 158744-40-2
• Molecular Formula: C₂₁H₃₁NO₅
• Molecular Weight: 377.481

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

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

Chemical Property:

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

There total 3 articles about Ethyl 4(S)-benzyl-3-(tert-butoxycarbonyl)-2,2-dimethyl-5(R)-oxazolidineacetate 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: 80.0%

N-(tert-butoxycarbonyl)-4(S)-amino-3(R)-hydroxy-5-phenylpentanoic acid ethyl ester (72155-47-6) + 2,2-dimethoxy-propane (77-76-9) → Ethyl 4(S)-benzyl-3-(tert-butoxycarbonyl)-2,2-dimethyl-5(R)-oxazolidineacetate (158744-40-2)

Guidance literature:

With toluene-4-sulfonic acid; 1.) r.t., 24 h, 2.) 50 deg C, 7 h;

DOI:10.1021/jo00092a026

Reference yield:

N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) → Ethyl 4(S)-benzyl-3-(tert-butoxycarbonyl)-2,2-dimethyl-5(R)-oxazolidineacetate (158744-40-2)

Guidance literature:

Multi-step reaction with 3 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

With 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) → Ethyl 4(S)-benzyl-3-(tert-butoxycarbonyl)-2,2-dimethyl-5(R)-oxazolidineacetate (158744-40-2)

Guidance literature:

Multi-step reaction with 2 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

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

DOI:10.1021/jo00092a026

upstream raw materials:

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

2,2-dimethoxy-propane

N-tert-butoxycarbonyl-L-phenylalanine

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

Downstream raw materials:

(4S,5R)-4-Benzyl-2,2-dimethyl-5-(2-oxo-ethyl)-oxazolidine-3-carboxylic acid tert-butyl ester

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

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

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