2-((R)-1-{[2-((R)-1-{[2-((R)-1-tert-Butoxycarbonylamino-1-methoxycarbonyl-ethyl)-5-methyl-oxazole-4-carbonyl]-amino}-1-methoxycarbonyl-ethyl)-5-methyl-oxazole-4-carbonyl]-amino}-1-methoxycarbonyl-ethyl)-5-methyl-oxazole-4-carboxylic acid benzyl ester

Base Information

• Chemical Name: 2-((R)-1-{[2-((R)-1-{[2-((R)-1-tert-Butoxycarbonylamino-1-methoxycarbonyl-ethyl)-5-methyl-oxazole-4-carbonyl]-amino}-1-methoxycarbonyl-ethyl)-5-methyl-oxazole-4-carbonyl]-amino}-1-methoxycarbonyl-ethyl)-5-methyl-oxazole-4-carboxylic acid benzyl ester
• CAS No.: 294181-89-8
• Molecular Formula: C₃₉H₄₆N₆O₁₅
• Molecular Weight: 838.825

Synonyms:

Chemical Property of 2-((R)-1-{[2-((R)-1-{[2-((R)-1-tert-Butoxycarbonylamino-1-methoxycarbonyl-ethyl)-5-methyl-oxazole-4-carbonyl]-amino}-1-methoxycarbonyl-ethyl)-5-methyl-oxazole-4-carbonyl]-amino}-1-methoxycarbonyl-ethyl)-5-methyl-oxazole-4-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-((R)-1-{[2-((R)-1-{[2-((R)-1-tert-Butoxycarbonylamino-1-methoxycarbonyl-ethyl)-5-methyl-oxazole-4-carbonyl]-amino}-1-methoxycarbonyl-ethyl)-5-methyl-oxazole-4-carbonyl]-amino}-1-methoxycarbonyl-ethyl)-5-methyl-oxazole-4-carboxylic acid benzyl ester

There total 6 articles about 2-((R)-1-{[2-((R)-1-{[2-((R)-1-tert-Butoxycarbonylamino-1-methoxycarbonyl-ethyl)-5-methyl-oxazole-4-carbonyl]-amino}-1-methoxycarbonyl-ethyl)-5-methyl-oxazole-4-carbonyl]-amino}-1-methoxycarbonyl-ethyl)-5-methyl-oxazole-4-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:

dimethyl 2-(tert-butoxycarbonylamino)malonate (61172-70-1) → 2-((R)-1-{[2-((R)-1-{[2-((R)-1-tert-Butoxycarbonylamino-1-methoxycarbonyl-ethyl)-5-methyl-oxazole-4-carbonyl]-amino}-1-methoxycarbonyl-ethyl)-5-methyl-oxazole-4-carbonyl]-amino}-1-methoxycarbonyl-ethyl)-5-methyl-oxazole-4-carboxylic acid benzyl ester (294181-89-8)

Guidance literature:

Multi-step reaction with 6 steps

1.1: MeONa

2.1: porcine liver esterase / acetonitrile; aq. phosphate buffer / pH 7

3.1: 95 percent / diphenylphosphoryl azide; iPr₂NEt / dimethylformamide / 20 h / 0 °C

4.1: Dess-Martin periodinane

4.2: 65 percent / Ph₃P; I₂; Et₃N

5.1: H₂ / Pd-hydroxide / ethanol; acetic acid

6.1: PyBOP; iPr₂NEt / dimethylformamide / 24 h / 20 °C

With porcine liver esterase; diphenylphosphoranyl azide; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; hydrogen; sodium methylate; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; palladium dihydroxide; In phosphate buffer; ethanol; acetic acid; N,N-dimethyl-formamide; acetonitrile; 1.1: Methylation / 2.1: Hydrolysis / 3.1: Acylation / 4.1: Oxidation / 4.2: cyclodehydration / 5.1: Hydrogenolysis / 6.1: Acylation;

DOI:10.1016/S0040-4039(00)00796-6

Reference yield:

dimethyl 2-[(tert-butoxycarbonyl)amino]-2-methylmalonate (150021-68-4) → 2-((R)-1-{[2-((R)-1-{[2-((R)-1-tert-Butoxycarbonylamino-1-methoxycarbonyl-ethyl)-5-methyl-oxazole-4-carbonyl]-amino}-1-methoxycarbonyl-ethyl)-5-methyl-oxazole-4-carbonyl]-amino}-1-methoxycarbonyl-ethyl)-5-methyl-oxazole-4-carboxylic acid benzyl ester (294181-89-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: porcine liver esterase / acetonitrile; aq. phosphate buffer / pH 7

2.1: 95 percent / diphenylphosphoryl azide; iPr₂NEt / dimethylformamide / 20 h / 0 °C

3.1: Dess-Martin periodinane

3.2: 65 percent / Ph₃P; I₂; Et₃N

4.1: H₂ / Pd-hydroxide / ethanol; acetic acid

5.1: PyBOP; iPr₂NEt / dimethylformamide / 24 h / 20 °C

With porcine liver esterase; diphenylphosphoranyl azide; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; hydrogen; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; palladium dihydroxide; In phosphate buffer; ethanol; acetic acid; N,N-dimethyl-formamide; acetonitrile; 1.1: Hydrolysis / 2.1: Acylation / 3.1: Oxidation / 3.2: cyclodehydration / 4.1: Hydrogenolysis / 5.1: Acylation;

DOI:10.1016/S0040-4039(00)00796-6

Reference yield:

(R)-2-tert-Butoxycarbonylamino-2-methyl-malonic acid monomethyl ester (150021-55-9) → 2-((R)-1-{[2-((R)-1-{[2-((R)-1-tert-Butoxycarbonylamino-1-methoxycarbonyl-ethyl)-5-methyl-oxazole-4-carbonyl]-amino}-1-methoxycarbonyl-ethyl)-5-methyl-oxazole-4-carbonyl]-amino}-1-methoxycarbonyl-ethyl)-5-methyl-oxazole-4-carboxylic acid benzyl ester (294181-89-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 95 percent / diphenylphosphoryl azide; iPr₂NEt / dimethylformamide / 20 h / 0 °C

2.1: Dess-Martin periodinane

2.2: 65 percent / Ph₃P; I₂; Et₃N

3.1: H₂ / Pd-hydroxide / ethanol; acetic acid

4.1: PyBOP; iPr₂NEt / dimethylformamide / 24 h / 20 °C

With diphenylphosphoranyl azide; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; hydrogen; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; palladium dihydroxide; In ethanol; acetic acid; N,N-dimethyl-formamide; 1.1: Acylation / 2.1: Oxidation / 2.2: cyclodehydration / 3.1: Hydrogenolysis / 4.1: Acylation;

DOI:10.1016/S0040-4039(00)00796-6

upstream raw materials:

2-(1-tert-butoxycarbonylamino-1-methoxycarbonyl-ethyl)-5-methyl-oxazole-4-carboxylic acid

dimethyl 2-(tert-butoxycarbonylamino)malonate

(R)-2-tert-Butoxycarbonylamino-2-methyl-malonic acid monomethyl ester

dimethyl 2-[(tert-butoxycarbonyl)amino]-2-methylmalonate

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