(4S,7R,9S,13Z,16S)-4,8-bis[(tert-butyldimethylsilyl)oxy]-5,5,7,9,13-pentamethyl-16-[(1E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadec-13-ene-2,6-dione

• ChemBase ID: 162217
• Molecular Formular: C39H69NO5SSi2
• Molecular Mass: 720.20486
• Monoisotopic Mass: 719.44349838
• SMILES: C\1(=C\C[C@H](OC(=O)C[C@@H](C(C(=O)[C@@H](C([C@H](CCC1)C)O[Si](C(C)(C)C)(C)C)C)(C)C)O[Si](C(C)(C)C)(C)C)/C(=C/c1csc(n1)C)/C)/C
• Canonical SMILES: O=C1O[C@@H](C/C=C(/C)\CCC[C@@H](C([C@H](C(=O)C([C@H](C1)O[Si](C(C)(C)C)(C)C)(C)C)C)O[Si](C(C)(C)C)(C)C)C)/C(=C/c1csc(n1)C)/C
• InChI: InChI=1S/C39H69NO5SSi2/c1-26-19-18-20-27(2)35(45-48(16,17)38(9,10)11)29(4)36(42)39(12,13)33(44-47(14,15)37(6,7)8)24-34(41)43-32(22-21-26)28(3)23-31-25-46-30(5)40-31/h21,23,25,27,29,32-33,35H,18-20,22,24H2,1-17H3/b26-21-,28-23+/t27-,29+,32-,33-,35?/m0/s1
• InChIKey: BIYYEQKEADNAJH-BULOOIBFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S,7R,9S,13Z,16S)-4,8-bis[(tert-butyldimethylsilyl)oxy]-5,5,7,9,13-pentamethyl-16-[(1E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadec-13-ene-2,6-dione
• IUPAC Traditional name: (4S,7R,9S,13Z,16S)-4,8-bis[(tert-butyldimethylsilyl)oxy]-5,5,7,9,13-pentamethyl-16-[(1E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadec-13-ene-2,6-dione
• Synonyms: [4S-[4R*,7S*,8R*,9R*,13Z,16R*(E)]]-4,8-Bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-5,5,7,9,13-pentamethyl-16-[1-methyl-2-(2-methyl-4-thiazolyl)ethenyl]oxacyclohexadec-13-ene-2,6-dione; (4S,7R,8S,9S,13Z,16S)-4,8-Bis-{[tert-butyl(dimethyl)silyl]oxy}-5,5,7,9,13-pentamethyl-16-[(E)-1-methyl-2-(2-methyl-1,3-thiazol-4-yl)ethenyl]oxocyclohexadec-13-ene-2,6-dione

Database IDs

• CAS Number: 189453-35-8
• PubChem SID: 162256352
• PubChem CID: 45038362

CALCULATED PROPERTIES

• Acid pKa: 18.837952
• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): 10.734878
• LogD (pH = 7.4): 10.735591
• Log P: 10.7356
• Molar Refractivity: 195.7393 cm^3
• Polarizability: 81.263824 Å^3
• Polar Surface Area: 74.72 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

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

DETAILS

Toronto Research Chemicals - B415780

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)