4-[(1E,3S,5Z,10S)-8-(benzenesulfonyl)-3,11-bis[(tert-butyldimethylsilyl)oxy]-2,6,10-trimethylundeca-1,5-dien-1-yl]-2-methyl-1,3-thiazole

• ChemBase ID: 162222
• Molecular Formular: C36H61NO4S2Si2
• Molecular Mass: 692.17484
• Monoisotopic Mass: 691.3580545
• SMILES: c1(scc(n1)/C=C(/[C@@H](O[Si](C(C)(C)C)(C)C)C/C=C(\CC(C[C@@H](CO[Si](C(C)(C)C)(C)C)C)S(=O)(=O)c1ccccc1)/C)\C)C
• Canonical SMILES: C[C@@H](CC(S(=O)(=O)c1ccccc1)C/C(=C\C[C@@H](/C(=C/c1csc(n1)C)/C)O[Si](C(C)(C)C)(C)C)/C)CO[Si](C(C)(C)C)(C)C
• InChI: InChI=1S/C36H61NO4S2Si2/c1-27(20-21-34(41-45(13,14)36(8,9)10)29(3)24-31-26-42-30(4)37-31)22-33(43(38,39)32-18-16-15-17-19-32)23-28(2)25-40-44(11,12)35(5,6)7/h15-20,24,26,28,33-34H,21-23,25H2,1-14H3/b27-20-,29-24+/t28-,33?,34-/m0/s1
• InChIKey: YKXYTSHOAIXBSR-COVLIRCOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[(1E,3S,5Z,10S)-8-(benzenesulfonyl)-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)-8-(benzenesulfonyl)-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-8-(phenylsulfonyl)-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-8-(phenylsulfonyl)undeca-1,5-dienyl]-2-methyl-1,3-thiazole

Database IDs

• CAS Number: 308357-81-5
• PubChem SID: 162256357
• PubChem CID: 11146857

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): 9.162178
• LogD (pH = 7.4): 9.16289
• Log P: 9.1629
• Molar Refractivity: 188.0242 cm^3
• Polarizability: 78.31132 Å^3
• Polar Surface Area: 65.49 Å^2
• Rotatable Bonds: 17
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

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

DETAILS

Toronto Research Chemicals - B415850

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)