(3S,7R,8S,9S,12Z,15S,16E)-3,8-bis[(tert-butyldimethylsilyl)oxy]-15-hydroxy-4,4,7,9,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)-6-oxoheptadeca-12,16-dienoic acid

• ChemBase ID: 162216
• Molecular Formular: C39H71NO6SSi2
• Molecular Mass: 738.22014
• Monoisotopic Mass: 737.45406306
• SMILES: c1(scc(n1)/C=C(/[C@H](C/C=C(\CC[C@@H]([C@@H]([C@H](C(=O)CC([C@H](CC(=O)O)O[Si](C(C)(C)C)(C)C)(C)C)C)O[Si](C(C)(C)C)(C)C)C)/C)O)\C)C
• Canonical SMILES: OC(=O)C[C@@H](C(CC(=O)[C@@H]([C@H]([C@H](CC/C(=C\C[C@@H](/C(=C/c1csc(n1)C)/C)O)/C)C)O[Si](C(C)(C)C)(C)C)C)(C)C)O[Si](C(C)(C)C)(C)C
• InChI: InChI=1S/C39H71NO6SSi2/c1-26(19-21-32(41)28(3)22-31-25-47-30(5)40-31)18-20-27(2)36(46-49(16,17)38(9,10)11)29(4)33(42)24-39(12,13)34(23-35(43)44)45-48(14,15)37(6,7)8/h19,22,25,27,29,32,34,36,41H,18,20-21,23-24H2,1-17H3,(H,43,44)/b26-19-,28-22+/t27-,29-,32-,34-,36-/m0/s1
• InChIKey: UAGRVQUVKGHDQE-XXLGVNKGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,7R,8S,9S,12Z,15S,16E)-3,8-bis[(tert-butyldimethylsilyl)oxy]-15-hydroxy-4,4,7,9,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)-6-oxoheptadeca-12,16-dienoic acid
• IUPAC Traditional name: (3S,7R,8S,9S,12Z,15S,16E)-3,8-bis[(tert-butyldimethylsilyl)oxy]-15-hydroxy-4,4,7,9,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)-6-oxoheptadeca-12,16-dienoic acid
• Synonyms: [3S-(3R*,6S*,7R*,8R*,12Z,15R*,16E)]-3,7-Bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-15-hydroxy-4,4,6,8,12,16-hexamethyl-17-(2-methyl-4-thiazolyl)-5-oxo-12,16-heptadecadienoic Acid; (3S,6R,7S,12Z,15S,16E)-3,7-Bis-{[tert-butyl(dimethyl)silyl]oxy}-15-hydroxy-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)-5-oxoheptadeca-12,16-dienoic Acid

Database IDs

• CAS Number: 193146-26-8
• PubChem SID: 162256351
• PubChem CID: 46783536

CALCULATED PROPERTIES

• Acid pKa: 4.2291327
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): 8.369174
• LogD (pH = 7.4): 6.6100564
• Log P: 9.466509
• Molar Refractivity: 199.1797 cm^3
• Polarizability: 82.36135 Å^3
• Polar Surface Area: 105.95 Å^2
• Rotatable Bonds: 21
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

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

DETAILS

Toronto Research Chemicals - B415725

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)