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Technology Process of Thiomarinol A

Thiomarinol A

Base Information
  • Chemical Name:Thiomarinol A
  • CAS No.:146697-04-3
  • Molecular Formula:C30H44N2O9S2
  • Molecular Weight:640.81
  • Hs Code.:
  • DSSTox Substance ID:DTXSID601098553
  • Nikkaji Number:J680.555H
  • Wikidata:Q27134758
  • Mol file:146697-04-3.mol
Thiomarinol A

Synonyms:thiomarinol;thiomarinol A

Suppliers and Price of Thiomarinol A
Supply Marketing:
Business phase:
The product has achieved commercial mass production*data from LookChem market partment
Manufacturers and distributors:
  • Manufacture/Brand
  • Chemicals and raw materials
  • Packaging
  • price
  • American Custom Chemicals Corporation
  • THIOMARINOL 95.00%
  • 5MG
  • $ 498.27
Total 13 raw suppliers
Chemical Property of Thiomarinol A
Chemical Property:
  • PSA：238.64000 
  • LogP:4.49400 
  • XLogP3:2
  • Hydrogen Bond Donor Count:6
  • Hydrogen Bond Acceptor Count:11
  • Rotatable Bond Count:17
  • Exact Mass:640.24882333
  • Heavy Atom Count:43
  • Complexity:1120
Purity/Quality:

99% *data from raw suppliers

THIOMARINOL 95.00% *data from reagent suppliers

Safty Information:
  • Pictogram(s):  
  • Hazard Codes: 
MSDS Files:
Useful:
  • Canonical SMILES:CC(C=CCC1COC(C(C1O)O)C(C(=CC(=O)OCCCCCCCC(=O)NC2=C3C(=CSS3)NC2=O)C)O)C(C)O
  • Isomeric SMILES:C[C@H](/C=C/C[C@H]1CO[C@H]([C@@H]([C@@H]1O)O)[C@@H](/C(=C/C(=O)OCCCCCCCC(=O)NC2=C3C(=CSS3)NC2=O)/C)O)[C@H](C)O
  • General Description Thiomarinol is a marine-derived antibiotic characterized by a complex structure that includes a 2,3,4,5-tetrasubstituted tetrahydropyran core, a feature shared with pseudomonic acid antibiotics. This structural motif is critical for its bioactivity, and synthetic efforts, such as the intramolecular oxy-Michael (IMOM) strategy, have been developed to efficiently construct this core segment for the total synthesis of thiomarinol.
Refernces

Diastereoselective construction of substituted tetrahydropyrans using an intramolecular oxy-Michael strategy

10.1016/j.tetlet.2009.01.084

The research focuses on the highly diastereoselective construction of substituted tetrahydropyrans, which are a common core segment of thiomarinols and pseudomonic acid antibiotics. The purpose of this study was to develop an efficient methodology for the synthesis of the C3–C10 segment containing the tetrahydropyran ring, using an intramolecular oxy-Michael (IMOM) reaction under both basic and high-pressure conditions. The key chemicals used in the process include hydroxy enoates, epoxy alcohols, and various reagents for the IMOM reaction, such as NaH, TBAF, and Hünig’s base (iPr2NEt). The study successfully demonstrated that the IMOM reaction of epoxy hydroxy Z-enoate under these conditions led to the formation of the tetrasubstituted tetrahydropyran core structure with high diastereoselectivity, marking the first efficient accomplishment of the IMOM reaction for assembling substituted tetrahydropyrans under high-pressure conditions. The conclusions drawn from the research highlight the efficiency of the developed protocol for synthesizing the 2,3,4,5-tetrasubstituted tetrahydropyran core structure, which is crucial for the total synthesis of thiomarinols and pseudomonic acid antibiotics.

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