(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetyloxy)-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-9,12,15-tris[(triethylsilyl)oxy]-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl (2E)-2-methylbut-2-enoate

• ChemBase ID: 179300
• Molecular Formular: C45H80O10Si3
• Molecular Mass: 865.3672
• Monoisotopic Mass: 864.50592836
• SMILES: C1(=C2C([C@@](C[C@@H]1O[Si](CC)(CC)CC)([C@H]([C@H]1[C@](C(=O)[C@@H]2O[Si](CC)(CC)CC)([C@H](C[C@@H]2[C@]1(CO2)OC(=O)C)O[Si](CC)(CC)CC)C)OC(=O)/C(=C/C)/C)O)(C)C)C
• Canonical SMILES: C/C=C(/C(=O)O[C@H]1[C@@H]2[C@@]3(CO[C@@H]3C[C@@H]([C@@]2(C)C(=O)[C@@H](C2=C([C@H](C[C@]1(O)C2(C)C)O[Si](CC)(CC)CC)C)O[Si](CC)(CC)CC)O[Si](CC)(CC)CC)OC(=O)C)\C
• InChI: InChI=1S/C45H80O10Si3/c1-17-30(11)41(48)51-40-38-43(16,34(54-57(21-5,22-6)23-7)27-35-44(38,29-50-35)52-32(13)46)39(47)37(55-58(24-8,25-9)26-10)36-31(12)33(28-45(40,49)42(36,14)15)53-56(18-2,19-3)20-4/h17,33-35,37-38,40,49H,18-29H2,1-16H3/b30-17+/t33-,34-,35+,37+,38-,40-,43+,44-,45+/m0/s1
• InChIKey: KWOZPKDHVQAPHU-OTGBLBQLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetyloxy)-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-9,12,15-tris[(triethylsilyl)oxy]-6-oxatetracyclo[11.3.1.0^3,^1^0.0^4,^7]heptadec-13-en-2-yl (2E)-2-methylbut-2-enoate
• IUPAC Traditional name: (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetyloxy)-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-9,12,15-tris[(triethylsilyl)oxy]-6-oxatetracyclo[11.3.1.0^3,^1^0.0^4,^7]heptadec-13-en-2-yl (2E)-2-methylbut-2-enoate
• Synonyms: (2E)-2-Methyl-2-butenoic Acid (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-12b-(acetyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-4,6,9-tri-O-triethylsilyl-11-hydroxy-4a,8,13,13-tetramethyl-5-oxo-7,11-methano-1H-cyclodeca[3,4]benz[1,2-b]oxet-12-yl Ester; 7,10,13-Tri-(O-triethylsilyl) 2-Debenzoyl-2-tigloyl 10-Deacetyl Baccatin III

Database IDs

• PubChem SID: 164235210
• PubChem CID: 71752858

CALCULATED PROPERTIES

• Acid pKa: 13.272561
• H Acceptors: 8
• H Donor: 1
• LogD (pH = 5.5): 9.4097
• LogD (pH = 7.4): 9.409699
• Log P: 9.4097
• Molar Refractivity: 221.0698 cm^3
• Polarizability: 94.03041 Å^3
• Polar Surface Area: 126.82 Å^2
• Rotatable Bonds: 20
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ehtyl Acetate

DETAILS

Toronto Research Chemicals - T886600

Protected analog of 10-Deacetylbaccatin III (D198250).

REFERENCES

• Gabetta, B., et al.: J. Natural Products, 58, 1508 (1995)