4-[(1E,3S,5Z,10S)-3,11-bis[(tert-butyldimethylsilyl)oxy]-2,6,10-trimethylundeca-1,5-dien-1-yl]-2-methyl-1,3-thiazole

• ChemBase ID: 162223
• Molecular Formular: C30H57NO2SSi2
• Molecular Mass: 552.01508
• Monoisotopic Mass: 551.36485413
• SMILES: c1(scc(n1)/C=C(/[C@@H](O[Si](C(C)(C)C)(C)C)C/C=C(\CCC[C@@H](CO[Si](C(C)(C)C)(C)C)C)/C)\C)C
• Canonical SMILES: C[C@H](CO[Si](C(C)(C)C)(C)C)CCC/C(=C\C[C@@H](/C(=C/c1csc(n1)C)/C)O[Si](C(C)(C)C)(C)C)/C
• InChI: InChI=1S/C30H57NO2SSi2/c1-23(16-15-17-24(2)21-32-35(11,12)29(5,6)7)18-19-28(33-36(13,14)30(8,9)10)25(3)20-27-22-34-26(4)31-27/h18,20,22,24,28H,15-17,19,21H2,1-14H3/b23-18-,25-20+/t24-,28-/m0/s1
• InChIKey: VTUYIQLTBSOSCD-SKTKRZFLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[(1E,3S,5Z,10S)-3,11-bis[(tert-butyldimethylsilyl)oxy]-2,6,10-trimethylundeca-1,5-dien-1-yl]-2-methyl-1,3-thiazole
• IUPAC Traditional name: 4-[(1E,3S,5Z,10S)-3,11-bis[(tert-butyldimethylsilyl)oxy]-2,6,10-trimethylundeca-1,5-dien-1-yl]-2-methyl-1,3-thiazole
• Synonyms: 4-[(1E,3S,5Z,10S)-3,11-Bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2,6,10-trimethyl-1,5-undecadien-1-yl]-2-methyl-thiazole; 4-[(1E,3S,5Z,8R/S,10S)-3,11-Bis-{[tert-butyl(dimethyl)silyl]oxy}-2,6,10-trimethyl-undeca-1,5-dienyl]-2-methyl-1,3-thiazole

Database IDs

• CAS Number: 210690-85-0
• PubChem SID: 162256358
• PubChem CID: 10984480

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 8.887678
• LogD (pH = 7.4): 8.888391
• Log P: 8.8884
• Molar Refractivity: 154.7204 cm^3
• Polarizability: 64.59125 Å^3
• Polar Surface Area: 31.35 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ethanol; Ethyl Acetate; Methanol; Toluene
• Apperance: Colourless Oil

DETAILS

Toronto Research Chemicals - B415890

An intermediate in the synthesis of Epothilones. Epothilones are polyketide natural products that inhibit cancer cells by a mechanism similar to paclitaxel, and also are effective against paclitaxel-resistant tumours. Epothilone D is in phase I clinical

REFERENCES

• Hoee, G., et al.: Pure Appl. Chem., 71, 11, 2019 (1999)
• Giannakakou, P., et al.: Proc. Natl. Acad. Sci. USA, 97, 2904 (2000)