Platensimycin

Base Information

• Chemical Name: Platensimycin
• CAS No.: 835876-32-9
• Deprecated CAS: 898249-77-9
• Molecular Formula: C24H27NO7
• Molecular Weight: 441.481
• UNII: Q3DQ78KOFY
• DSSTox Substance ID: DTXSID80894888
• Nikkaji Number: J2.310.958A
• Wikipedia: Platensimycin
• Wikidata: Q423275
• Metabolomics Workbench ID: 102087
• ChEMBL ID: CHEMBL411278
• Mol file: 835876-32-9.mol

Synonyms:platensimycin

Chemical Property of Platensimycin

Chemical Property:

• PSA: 136.65000
• LogP: 3.88320
• Storage Temp.: ?20°C
• Solubility.: DMSO: soluble1mg/mL, clear, colorless
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 5
• Exact Mass: 441.17875220
• Heavy Atom Count: 32
• Complexity: 888

Purity/Quality:

HPLC≥98% ^*data from raw suppliers

Platensimycin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CC34CC1CC(C3C(C(=O)C=C4)(C)CCC(=O)NC5=C(C=CC(=C5O)C(=O)O)O)O2
• Isomeric SMILES: C[C@]12C[C@]34C[C@H]1C[C@@H]([C@H]3[C@](C(=O)C=C4)(C)CCC(=O)NC5=C(C=CC(=C5O)C(=O)O)O)O2
• Uses: Platensimycin is a novel, broad spectrum, Gram-positive antibiotic produced by strains of Streptomyces platensis. Its discovery was heralded by high profile publication and commentary in the scientific and lay press. Platensimycin was discovered by a target-based, whole-cell screening strategy using an antisense differential sensitivity assay, based on the inhibition of fatty acid synthesis. Platensimycin inhibits bacterial growth by selectively inhibiting the elongation enzyme, b-ketoacyl acyl carrier protein synthase (FabF) of the fatty acid synthesis pathway. Platensimycin is a broad spectrum gram-positive antibiotic.

Technology Process of Platensimycin

There total 17 articles about Platensimycin 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: 85.0%

C29H39NO7Si (1109175-39-4) → (-)-platensimycin (835876-32-9)

Guidance literature:

With tris(dimethylamino)sulfonium trimethylsilyldifluoride; In N,N-dimethyl-formamide; at 40 ℃; for 1h;

DOI:10.1021/jo802261f

Reference yield: 63.0%

platensimycin methyl ester (948914-61-2) → (-)-platensimycin (835876-32-9)

Guidance literature:

platensimycin methyl ester; With water; potassium hydroxide; In 1,4-dioxane; at 35 ℃; for 12h;

With hydrogenchloride; In 1,4-dioxane; water;

Reference yield:

C13H18INO2S (1041186-48-4) → (-)-platensimycin (835876-32-9)

Guidance literature:

Multi-step reaction with 13 steps

1.1: potassium hydroxide; water / methanol / 0 - 20 °C

1.2: 0 °C

2.1: triethylamine / diethyl ether / -20 °C

3.1: diethyl ether / -20 - 0 °C

4.1: dirhodium tetraacetate / dichloromethane / 10 h

5.1: 1-ethyl-piperidine; hypophosphorous acid / water; methanol / 0.17 h / 0 °C

5.2: 0 - 20 °C

6.1: N-ethyl-N,N-diisopropylamine; lithium chloride / acetonitrile / 0.25 h / 0 °C

6.2: 0 - 20 °C

7.1: Dimethylphenylsilane / Wilkinson's catalyst / toluene / 20 - 60 °C

7.2: 1 h / -40 °C

7.3: 1 h / 0 °C

8.1: toluene-4-sulfonic acid / toluene / 2 h / Reflux; Dean-Stark trap

9.1: N,N,N,N,N,N-hexamethylphosphoric triamide; potassium hexamethylsilazane / toluene; tetrahydrofuran / 0.5 h / -78 °C

9.2: 1 h / -10 °C

10.1: potassium hydroxide; tert-butyl alcohol / 0.08 h / 60 °C

10.2: 14 h / 60 °C

11.1: potassium hydroxide; water / methanol / 2 h / Reflux

11.2: 20 °C

12.1: triethylamine; HATU / N,N-dimethyl-formamide / 15 h / 24 °C

13.1: potassium hydroxide; water / 1,4-dioxane / 12 h / 35 °C

With 1-ethyl-piperidine; N,N,N,N,N,N-hexamethylphosphoric triamide; Dimethylphenylsilane; water; hypophosphorous acid; potassium hexamethylsilazane; toluene-4-sulfonic acid; triethylamine; N-ethyl-N,N-diisopropylamine; HATU; lithium chloride; potassium hydroxide; tert-butyl alcohol; dirhodium tetraacetate; Wilkinson's catalyst; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;

upstream raw materials:

C₂₉H₃₉NO₇Si

platensimycin methyl ester

C₁₃H₁₈INO₂S

C₁₀H₁₀IN₃O₂

Downstream raw materials:

C₂₅H₃₁NO₇

Refernces

• 1、 Ghosh, Arun K.,Xi, Kai. "Total synthesis of (-)-platensimycin, a novel antibacterial agent". experimental part. p. 1163 - 1170. Retrieved 2009/08/15.