(-)-3-N-(4,5-diphenyl-4-oxazolin-2-onyl)aminocardicinic acid tert-butyl ester

Base Information

• Chemical Name: (-)-3-N-(4,5-diphenyl-4-oxazolin-2-onyl)aminocardicinic acid tert-butyl ester
• CAS No.: 110207-46-0
• Molecular Formula: C₃₇H₃₄N₂O₆
• Molecular Weight: 602.687
• Mol file: 110207-46-0.mol

Synonyms:(-)-3-N-(4,5-diphenyl-4-oxazolin-2-onyl)aminocardicinic acid tert-butyl ester

Chemical Property of (-)-3-N-(4,5-diphenyl-4-oxazolin-2-onyl)aminocardicinic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-3-N-(4,5-diphenyl-4-oxazolin-2-onyl)aminocardicinic acid tert-butyl ester

There total 4 articles about (-)-3-N-(4,5-diphenyl-4-oxazolin-2-onyl)aminocardicinic acid tert-butyl 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: 96.0%

tert-butyl N-(4,5-diphenyl-4-oxazolin-2-onyl)-L-seryl-D-glycinate (111216-46-7) → (-)-3-N-(4,5-diphenyl-4-oxazolin-2-onyl)aminocardicinic acid tert-butyl ester (110207-46-0)

Guidance literature:

With diethylazodicarboxylate; triethyl phosphite; In tetrahydrofuran; at 20 ℃; for 12h; Darkness;

DOI:10.1021/jo4007893

Reference yield: 69.0%

D-glycine tert-butyl ester toluenesulfonate salt (123004-72-8) + L-Ox-serine dicyclohexylammonium salt (40719-42-4) → (-)-3-N-(4,5-diphenyl-4-oxazolin-2-onyl)aminocardicinic acid tert-butyl ester (110207-46-0)

Guidance literature:

L-Ox-serine dicyclohexylammonium salt; With (benzotriazol-1-yloxy)tripyrrolodinophosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 0 ℃; for 0.0166667h;

D-glycine tert-butyl ester toluenesulfonate salt; With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 3h;

DOI:10.1021/jo4007893

Reference yield:

L-Ox-serine dicyclohexylammonium salt → (-)-3-N-(4,5-diphenyl-4-oxazolin-2-onyl)aminocardicinic acid tert-butyl ester (110207-46-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / hydroxybenzotriazole monohydrate, dicyclohexylcarbodiimide / dimethylformamide; CH₂Cl₂ / 1.) 0 deg C, 2.5 h, 2.) RT, 1.5 h

2: 84 percent / triethyl phosphite, diethyl azodicarboxylate / tetrahydrofuran / 4.5 h

With benzotriazol-1-ol; dicyclohexyl-carbodiimide; diethylazodicarboxylate; triethyl phosphite; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja00158a040

upstream raw materials:

tert-butyl N-(4,5-diphenyl-4-oxazolin-2-onyl)-L-seryl-D-glycinate

D-2-[p-(benzyloxy)phenyl]glycine

D-glycine tert-butyl ester toluenesulfonate salt

L-Ox-serine dicyclohexylammonium salt

Downstream raw materials:

(-)-tert-butyl 3-aminonocardicinate hydrochloride

(-)-nocardicin G

(R)-{(S)-3-[(R)-2-tert-Butoxycarbonylamino-2-(4-hydroxy-phenyl)-acetylamino]-2-oxo-azetidin-1-yl}-(4-hydroxy-phenyl)-acetic acid tert-butyl ester

di-tert-butyl N-(tert-butoxycarbonyl)nocardicin D