Nocardicin A

Base Information

• Chemical Name: Nocardicin A
• CAS No.: 39391-39-4
• Molecular Formula: C23H24N4O9
• Molecular Weight: 500.465
• UNII: R76HLW7Z19
• DSSTox Substance ID: DTXSID201028178
• Nikkaji Number: J18.342C
• Wikipedia: Nocardicin_A
• Wikidata: Q4981302
• Metabolomics Workbench ID: 51012
• Mol file: 39391-39-4.mol

Synonyms:nocarcidins;nocardicin;nocardicin A;nocardicin A, sodium salt;nocardicin B

Chemical Property of Nocardicin A

Chemical Property:

• Melting Point: 214-216° (dec)
• Refractive Index: 1.6500 (estimate)
• Boiling Point: 591.34°C (rough estimate)
• PSA: 212.08000
• Density: 1.57g/cm³
• LogP: 0.93330
• XLogP3: -1.1
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 11
• Exact Mass: 500.15432836
• Heavy Atom Count: 36
• Complexity: 851

Purity/Quality:

99% ^*data from raw suppliers

Nocardicin A ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(=O)N1C(C2=CC=C(C=C2)O)C(=O)O)NC(=O)C(=NO)C3=CC=C(C=C3)OCCC(C(=O)O)N
• Isomeric SMILES: C1[C@@H](C(=O)N1[C@H](C2=CC=C(C=C2)O)C(=O)O)NC(=O)/C(=N\O)/C3=CC=C(C=C3)OCC[C@H](C(=O)O)N
• Uses: Nocardicin A is a β-lactam antibiotic.

Technology Process of Nocardicin A

There total 28 articles about Nocardicin A 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: 67.0%

di-tert-butyl N-(tert-butoxycarbonyl)nocardicin A (110269-45-9,110207-52-8) → (-)-nocardicin B (60134-71-6,39391-39-4)

Guidance literature:

With trifluoroacetic acid; 2-hydroxyethanethiol; for 0.116667h; Ambient temperature;

DOI:10.1021/ja00158a040

Reference yield: 67.0%

di-tert-butyl N-(tert-butoxycarbonyl)nocardicin A (110269-45-9,110207-52-8) → (-)-nocardicin A (39391-39-4)

Guidance literature:

With trifluoroacetic acid; 2-hydroxyethanethiol; for 0.116667h; Ambient temperature;

DOI:10.1016/S0040-4039(00)83888-5

Reference yield:

(R)-2-(((benzyloxy)carbonyl)amino)-2-(4-hydroxyphenyl)acetic acid (26787-75-7) → (-)-nocardicin B (60134-71-6,39391-39-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) potassium hydride / 1.) DMF, RT, 10 min, 2.) RT, 3 h

2: 88 percent / 2,6-lutidine, 1-hydroxybenzotriazole, dicyclohexylcarbodiimide / tetrahydrofuran / 1.) 0 deg C, 30 min, 2.) RT, 1.5 h

3: 98 percent / H₂ / 10percent Pd/C / ethanol / 3 h / 2068.6 Torr

4: 58 percent / sodium bicarbonate, sodium tungstate, hydrogen peroxide / H₂O; methanol / 6 h

5: 67 percent / 2-mercaptoethanol, trifluoroacetic acid / 0.12 h / Ambient temperature

With 2,6-dimethylpyridine; sodium tungstate; hydrogen; dihydrogen peroxide; potassium hydride; sodium hydrogencarbonate; benzotriazol-1-ol; dicyclohexyl-carbodiimide; trifluoroacetic acid; 2-hydroxyethanethiol; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; water;

DOI:10.1021/ja00158a040

upstream raw materials:

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

p-benzyloxybenzaldehyde

-propoxy>phenyl>glyoxylic acid

(3R)-α--3-bromo-N-(diphenylmethyl)-2-oxo-1-azetidineacetamide

Downstream raw materials:

D-4-hydroxyphenylglycine

cyclohexanecarboxylic acid-(4-bromo-phenacyl ester)

N,O-Bis(t-butoxycarbonyl)-3-amino-nocardicinsaure-(diphenylmethyl)ester

N-(t-Butoxycarbonyl)-3-amino-nocardicinsaure

Refernces

• 1、 Salituro, Gino M.,Townsend, Craig A.. "Total syntheses of (-)-nocardicins A-G: A biogenetic approach". . p. 760 - 770. Retrieved 2007/10/02.
• 2、 Isenring,Hofheinz. "A total synthesis of nocardicins". . p. 2591 - 2597. Retrieved 2007/10/02.