Platencin

Base Information

• Chemical Name: Platencin
• CAS No.: 869898-86-2
• Molecular Formula: C₂₄H₂₇NO₆
• Molecular Weight: 425.481
• UNII: XK356W8OOB
• ChEMBL ID: CHEMBL1092943
• Metabolomics Workbench ID: 106309
• Nikkaji Number: J2.462.373D
• Wikidata: Q27136732
• Mol file: 869898-86-2.mol

Synonyms:platencin

Chemical Property of Platencin

Chemical Property:

• Boiling Point: 670.1±55.0 °C(Predicted)
• PKA: 2.14±0.13(Predicted)
• Density: 1.38±0.1 g/cm3(Predicted)
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 425.18383758
• Heavy Atom Count: 31
• Complexity: 836

Purity/Quality:

98%Min ^*data from raw suppliers

Platencin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C2CC3CCC2(CC3=C)C=CC1=O)CCC(=O)NC4=C(C=CC(=C4O)C(=O)O)O
• Isomeric SMILES: C[C@@]1([C@@H]2C[C@@H]3CC[C@]2(CC3=C)C=CC1=O)CCC(=O)NC4=C(C=CC(=C4O)C(=O)O)O
• General Description: Platencin, also known by other names not specified in the abstract, is a recently discovered antibiotic with notable bioactivity and a structurally complex molecular framework, making it a significant target for synthetic efforts. A concise nine-step total synthesis of (-)-platencin has been achieved, highlighting its synthetic accessibility despite its intricate architecture.

Technology Process of Platencin

There total 70 articles about Platencin 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: 93.0%

platencin 2-(trimethylsilyl)ethyl ester (1020070-63-6) → (-)-platencin (869898-86-2)

Guidance literature:

With tris(dimethylamino)sulfonium trimethylsilyldifluoride; In N,N-dimethyl-formamide; at 40 ℃; for 0.666667h; Inert atmosphere;

DOI:10.1002/anie.200800066

Reference yield: 85.0%

C29H39NO6Si (1265279-45-5) → C24H27NO6 (1265278-78-1,869898-86-2)

Guidance literature:

With tris(dimethylamino)sulfonium trimethylsilyldifluoride; HATU; In N,N-dimethyl-formamide; at 23 - 40 ℃; for 1.33333h; Inert atmosphere;

DOI:10.1002/ejoc.201001281

Reference yield: 62.0%

3-amino-2,4-dihydroxybenzoic acid (860505-23-3) + 3-[(1RS,5RS,6SR,8RS)-5-methyl-9-methylidene-4-oxotricyclo[6.2.2.0(1,6)]dodec-2-en-5-yl]propanoic acid → (±)-platencin (869898-86-2)

Guidance literature:

3-[(1RS,5RS,6SR,8RS)-5-methyl-9-methylidene-4-oxotricyclo[6.2.2.0(1,6)]dodec-2-en-5-yl]propanoic acid; With dmap; triethylamine; dicyclohexyl-carbodiimide; In dichloromethane; acetonitrile; at 20 ℃; for 7h; Inert atmosphere;

3-amino-2,4-dihydroxybenzoic acid; In dichloromethane; N,N-dimethyl-formamide; acetonitrile; at 20 ℃; for 38h; Inert atmosphere;

DOI:10.1002/anie.200800756

upstream raw materials:

platencin 2-(trimethylsilyl)ethyl ester

3-amino-2,4-dihydroxybenzoic acid

3-[(1S,5S,6R,8S)-5-methyl-9-methylene-4-oxotricyclo[6.2.2.0(1,6)]-dodec-2-en-5-yl]propionic acid

(1R,6S,8S)-9-methylidenetricyclo[6.2.2.0(1,6)]dodec-2-en-4-one

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.