(4R,5R)-2-((S)-1-Benzyloxycarbonylamino-2-methyl-propyl)-5-methyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester

Base Information

• Chemical Name: (4R,5R)-2-((S)-1-Benzyloxycarbonylamino-2-methyl-propyl)-5-methyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester
• CAS No.: 267653-10-1
• Molecular Formula: C₁₈H₂₄N₂O₅
• Molecular Weight: 348.399
• Mol file: 267653-10-1.mol

Synonyms:(4R,5R)-2-((S)-1-Benzyloxycarbonylamino-2-methyl-propyl)-5-methyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester

Chemical Property of (4R,5R)-2-((S)-1-Benzyloxycarbonylamino-2-methyl-propyl)-5-methyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,5R)-2-((S)-1-Benzyloxycarbonylamino-2-methyl-propyl)-5-methyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester

There total 2 articles about (4R,5R)-2-((S)-1-Benzyloxycarbonylamino-2-methyl-propyl)-5-methyl-4,5-dihydro-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: 75.0%

(2R,3S)-2-((S)-2-Benzyloxycarbonylamino-3-methyl-butyrylamino)-3-hydroxy-butyric acid methyl ester → (4R,5R)-2-((S)-1-Benzyloxycarbonylamino-2-methyl-propyl)-5-methyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester (267653-10-1)

Guidance literature:

With Burgess Reagent; In tetrahydrofuran; at 70 - 75 ℃; for 1h;

DOI:10.1016/S0040-4020(00)00767-5

Reference yield: 72.0%

(R)-2-((S)-2-Benzyloxycarbonylamino-3-methyl-butyrylamino)-3-hydroxy-butyric acid methyl ester → (4R,5R)-2-((S)-1-Benzyloxycarbonylamino-2-methyl-propyl)-5-methyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester (267653-10-1)

Guidance literature:

With (bis-(2-methoxyethyl)amino)sulfur trufluoride; In dichloromethane; at -20 ℃; for 0.5h;

DOI:10.1021/ol005777b

Reference yield: 47.0%

(4R,5R)-2-((S)-1-Amino-2-methyl-propyl)-5-methyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester (892397-21-6) + (4R,5R)-2-((S)-1-Benzyloxycarbonylamino-2-methyl-propyl)-5-methyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester (267653-10-1) → (4R,5R)-methyl 2-((S)-1-((4S,5R)-2-((S)-1-(benzyloxycarbonylamino)-2-methylpropyl)-5-methyl-4,5-dihydrooxazole-4-carboxamido)-2-methylpropyl)-5-methyl-4,5-dihydrooxazole-4-carboxylate

Guidance literature:

(4R,5R)-2-((S)-1-Benzyloxycarbonylamino-2-methyl-propyl)-5-methyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester; With sodium hydroxide; In methanol; water; at 20 ℃; for 1.5h;

(4R,5R)-2-((S)-1-Amino-2-methyl-propyl)-5-methyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester; With diphenylphosphoranyl azide; sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃; for 48h;

DOI:10.1021/ol060677c

Downstream raw materials:

4-<2-(1-benzyloxycarbonylamino-2-methylpropyl)>-5-methyl-trans-oxazoline carboxylic acid

cyclo[γ-phenyl-allo-homoThr-D-Thr(oxaz)-Val-D-Thr(oxaz)-Val-D-Thr(oxaz)]

cyclo[γ-phenyl-allo-homoThr-D-Thr(oxaz)-Val-D-Thr(oxaz)-Val-D-Thr(oxaz)] pent-4-enoate

cyclo[γ-phenyl-allo-homoThr(TBDPS)-D-Thr(oxaz)-Val-D-Thr(oxaz)-Val-D-Thr(oxaz)]