5-((S)-1-Benzyloxycarbonylamino-2-hydroxy-ethyl)-oxazole-4-carboxylic acid methyl ester

Base Information

• Chemical Name: 5-((S)-1-Benzyloxycarbonylamino-2-hydroxy-ethyl)-oxazole-4-carboxylic acid methyl ester
• CAS No.: 81658-10-8
• Molecular Formula: C₁₅H₁₆N₂O₆
• Molecular Weight: 320.302

Synonyms:5-((S)-1-Benzyloxycarbonylamino-2-hydroxy-ethyl)-oxazole-4-carboxylic acid methyl ester

Chemical Property of 5-((S)-1-Benzyloxycarbonylamino-2-hydroxy-ethyl)-oxazole-4-carboxylic acid methyl ester

Chemical Property:

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Technology Process of 5-((S)-1-Benzyloxycarbonylamino-2-hydroxy-ethyl)-oxazole-4-carboxylic acid methyl ester

There total 2 articles about 5-((S)-1-Benzyloxycarbonylamino-2-hydroxy-ethyl)-oxazole-4-carboxylic acid methyl 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:

5-((S)-1-Benzyloxycarbonylamino-2-tert-butoxy-ethyl)-oxazole-4-carboxylic acid methyl ester (81658-09-5) → 5-((S)-1-Benzyloxycarbonylamino-2-hydroxy-ethyl)-oxazole-4-carboxylic acid methyl ester (81658-10-8)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; for 2h; Ambient temperature;

DOI:10.1016/S0040-4039(00)87057-4

Reference yield:

N-benzyloxycarbonyl-O-t-butyl-L-serine (1676-75-1) → 5-((S)-1-Benzyloxycarbonylamino-2-hydroxy-ethyl)-oxazole-4-carboxylic acid methyl ester (81658-10-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 62 percent / diphenyl phosphorazidate, K₂CO₃ sesquihydrate / dimethylformamide / 1.) 0 deg C, 2 h, 2.) room temp., 14 h

2: trifluoroacetic acid / CH₂Cl₂ / 2 h / Ambient temperature

With diphenyl phosphoryl azide; potassium carbonate; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)87057-4

Reference yield: 67.0%

pivaloyl chloride (3282-30-2) + 5-((S)-1-Benzyloxycarbonylamino-2-hydroxy-ethyl)-oxazole-4-carboxylic acid methyl ester (81658-10-8) → 5-[(S)-1-Benzyloxycarbonylamino-2-(2,2-dimethyl-propionyloxy)-ethyl]-oxazole-4-carboxylic acid methyl ester (81658-11-9)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 0 ℃; for 0.5h;

DOI:10.1016/S0040-4039(00)87057-4

upstream raw materials:

5-((S)-1-Benzyloxycarbonylamino-2-tert-butoxy-ethyl)-oxazole-4-carboxylic acid methyl ester

N-benzyloxycarbonyl-O-t-butyl-L-serine

Downstream raw materials:

5-[(S)-1-Benzyloxycarbonylamino-2-(2,2-dimethyl-propionyloxy)-ethyl]-oxazole-4-carboxylic acid methyl ester

{(R)-1-[(4S,5S)-5-((R)-2-Benzyloxycarbonylamino-propionylamino)-2,2-dimethyl-[1,3]dioxan-4-yl]-2-oxo-ethyl}-carbamic acid benzyl ester

{(S)-1-[(4S,5S)-5-((R)-2-Benzyloxycarbonylamino-propionylamino)-2,2-dimethyl-[1,3]dioxan-4-yl]-2-hydroxy-ethyl}-carbamic acid benzyl ester

2,2-Dimethyl-propionic acid (2S,3S,4S)-2-benzyloxycarbonylamino-4-((R)-2-benzyloxycarbonylamino-propionylamino)-3,5-dihydroxy-pentyl ester

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