(7S,11S,12S,16Z,19S)-7-[(tert-butyldimethylsilyl)oxy]-11-hydroxy-2,2,3,3,8,8,10,12,16,21,21,22,22-tridecamethyl-19-[(1E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-4,20-dioxa-3,21-disilatricos-16-en-9-one

• ChemBase ID: 179026
• Molecular Formular: C45H87NO5SSi3
• Molecular Mass: 838.49748
• Monoisotopic Mass: 837.56127548
• SMILES: C(=C\C[C@@H](/C(=C/c1csc(n1)C)/C)O[Si](C(C)(C)C)(C)C)(\CCC[C@@H]([C@@H](C(C(=O)C([C@H](CCO[Si](C(C)(C)C)(C)C)O[Si](C(C)(C)C)(C)C)(C)C)C)O)C)/C
• Canonical SMILES: CC([Si](O[C@H](C(C(=O)C([C@H]([C@H](CCC/C(=C\C[C@@H](/C(=C/c1csc(n1)C)/C)O[Si](C(C)(C)C)(C)C)/C)C)O)C)(C)C)CCO[Si](C(C)(C)C)(C)C)(C)C)(C)C
• InChI: InChI=1S/C45H87NO5SSi3/c1-32(26-27-38(50-54(19,20)43(9,10)11)34(3)30-37-31-52-36(5)46-37)24-23-25-33(2)40(47)35(4)41(48)45(15,16)39(51-55(21,22)44(12,13)14)28-29-49-53(17,18)42(6,7)8/h26,30-31,33,35,38-40,47H,23-25,27-29H2,1-22H3/b32-26-,34-30+/t33-,35?,38-,39-,40-/m0/s1
• InChIKey: XPWGOKRSLJTZLR-OSLNQJGMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (7S,11S,12S,16Z,19S)-7-[(tert-butyldimethylsilyl)oxy]-11-hydroxy-2,2,3,3,8,8,10,12,16,21,21,22,22-tridecamethyl-19-[(1E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-4,20-dioxa-3,21-disilatricos-16-en-9-one
• IUPAC Traditional name: (7S,11S,12S,16Z,19S)-7-[(tert-butyldimethylsilyl)oxy]-11-hydroxy-2,2,3,3,8,8,10,12,16,21,21,22,22-tridecamethyl-19-[(1E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-4,20-dioxa-3,21-disilatricos-16-en-9-one
• Synonyms: (3S,6R,7S,8S,12Z,15S,16E)-1,3,15-Tris-{[tert-butyl(dimethyl)silyl]oxy}-7-hydroxy-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)heptadecyl-12,16-dien-5-one

Database IDs

• CAS Number: 193146-49-5
• PubChem SID: 164234936
• PubChem CID: 71752743

CALCULATED PROPERTIES

• Acid pKa: 14.534954
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 12.587277
• LogD (pH = 7.4): 12.587991
• Log P: 12.588
• Molar Refractivity: 229.4533 cm^3
• Polarizability: 96.52479 Å^3
• Polar Surface Area: 77.88 Å^2
• Rotatable Bonds: 24
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

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

DETAILS

Toronto Research Chemicals - T876675

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)