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:

>95% by HPLC ^*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
• General Description: PlatensiMycin is a potent antibiotic effective against multi-resistant bacteria like MRSA and VRE, derived from a chiral synthetic intermediate through enantioselective synthesis involving catalytic asymmetric intramolecular cyclopropanation, enabling the development of its derivatives and analogs.

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

Enantioselective divergent approaches to both (-)-platensimycin and (-)-platencin

10.1016/j.tet.2010.10.076

The research aimed to develop enantioselective divergent approaches for the synthesis of (-)-platensimycin and (-)-platencin, two new class antibiotics with potent activity against multi-resistant bacteria such as MRSA and VRE. The researchers designed a chiral synthetic intermediate with a useful a,b-unsaturated sulfone functionality, which served as a masked ketone and a good Michael acceptor. This intermediate was prepared via a highly enantioselective catalytic asymmetric intramolecular cyclopropanation (CAIMCP) developed in their laboratory. The CAIMCP of a-diazo-b-keto sulfone with CuOTf and bisoxazoline ligand 6 successfully afforded cyclopropane derivatives with high enantiomeric excess. The key intermediate 11 was used to synthesize both (-)-platensimycin and (-)-platencin through different synthetic pathways. The formal enantioselective total syntheses of both compounds were achieved, proving the applicability of the uniquely functionalized tricyclo[4.4.0.0]decene derivative and the usefulness of the CAIMCP in natural product synthesis. The study concluded that the developed chiral intermediate enabled the total syntheses of both antibiotics and could be useful for preparing their new derivatives and congeners.

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