(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetyloxy)-1-hydroxy-15-{[(2R,3S)-2-hydroxy-3-{[({1-[(4-methoxyphenyl)methoxy]-2-methylpropan-2-yl}oxy)carbonyl]amino}-3-phenylpropanoyl]oxy}-10,14,17,17-tetramethyl-11-oxo-9,12-bis({[(2,2,2-trichloroethoxy)carbonyl]oxy})-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl benzoate

• ChemBase ID: 166936
• Molecular Formular: C57H63Cl6NO20
• Molecular Mass: 1294.82282
• Monoisotopic Mass: 1291.2074595
• SMILES: C1(=C2C([C@@](C[C@@H]1OC(=O)[C@@H]([C@@H](NC(=O)OC(COCc1ccc(cc1)OC)(C)C)c1ccccc1)O)([C@H]([C@H]1[C@](C(=O)[C@@H]2OC(=O)OCC(Cl)(Cl)Cl)([C@H](C[C@@H]2[C@]1(CO2)OC(=O)C)OC(=O)OCC(Cl)(Cl)Cl)C)OC(=O)c1ccccc1)O)(C)C)C
• Canonical SMILES: COc1ccc(cc1)COCC(OC(=O)N[C@H]([C@H](C(=O)O[C@H]1C[C@@]2(O)[C@@H](OC(=O)c3ccccc3)[C@H]3[C@@](C(=O)[C@@H](C(=C1C)C2(C)C)OC(=O)OCC(Cl)(Cl)Cl)(C)[C@@H](OC(=O)OCC(Cl)(Cl)Cl)C[C@@H]1[C@]3(CO1)OC(=O)C)O)c1ccccc1)(C)C
• InChI: InChI=1S/C57H63Cl6NO20/c1-30-36(79-47(69)41(66)40(33-15-11-9-12-16-33)64-48(70)84-51(3,4)26-75-25-32-19-21-35(74-8)22-20-32)24-55(73)45(82-46(68)34-17-13-10-14-18-34)43-53(7,44(67)42(39(30)52(55,5)6)81-50(72)78-29-57(61,62)63)37(80-49(71)77-28-56(58,59)60)23-38-54(43,27-76-38)83-31(2)65/h9-22,36-38,40-43,45,66,73H,23-29H2,1-8H3,(H,64,70)/t36-,37-,38+,40-,41+,42+,43-,45-,53+,54-,55+/m0/s1
• InChIKey: QEUAAIWYANCZDR-KRXHHQNQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetyloxy)-1-hydroxy-15-{[(2R,3S)-2-hydroxy-3-{[({1-[(4-methoxyphenyl)methoxy]-2-methylpropan-2-yl}oxy)carbonyl]amino}-3-phenylpropanoyl]oxy}-10,14,17,17-tetramethyl-11-oxo-9,12-bis({[(2,2,2-trichloroethoxy)carbonyl]oxy})-6-oxatetracyclo[11.3.1.0^3,^1^0.0^4,^7]heptadec-13-en-2-yl benzoate
• IUPAC Traditional name: (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetyloxy)-1-hydroxy-15-{[(2R,3S)-2-hydroxy-3-{[({1-[(4-methoxyphenyl)methoxy]-2-methylpropan-2-yl}oxy)carbonyl]amino}-3-phenylpropanoyl]oxy}-10,14,17,17-tetramethyl-11-oxo-9,12-bis({[(2,2,2-trichloroethoxy)carbonyl]oxy})-6-oxatetracyclo[11.3.1.0^3,^1^0.0^4,^7]heptadec-13-en-2-yl benzoate
• Synonyms: [2aR-[2aα,4β,4aβ,6β,9α(αR*,βS*),11α,12α,12aα,12bα]]-α-Hydroxy-β-[[[2-[(4-methoxyphenyl)methoxy]-1,1-dimethylethoxy]carbonyl]amino]benzenepropanoic Acid 12b-(Acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-11-hydroxy-4a,8,13,13-tetramethyl-5-oxo-4,6-bis[[(2,2,2-trichloroethoxy)carbonyl]oxy]-7,11-methano-1H-cyclodeca[3,4]benz[1,2-b]oxet-9-yl Ester; N-Des-t-boc-N-2-[2-methyl-1-(4-methoxyphenyl)methoxy]propyloxycarbonxyl-7,10-O-bis{[(2,2,2-trichloroethyl)oxy]carbonyl} Docetaxel

Database IDs

• CAS Number: 154044-74-3
• PubChem SID: 162261069
• PubChem CID: 15765784

CALCULATED PROPERTIES

• Acid pKa: 11.963473
• H Acceptors: 14
• H Donor: 3
• LogD (pH = 5.5): 9.350954
• LogD (pH = 7.4): 9.350943
• Log P: 9.350954
• Molar Refractivity: 302.7316 cm^3
• Polarizability: 120.29729 Å^3
• Polar Surface Area: 273.51 Å^2
• Rotatable Bonds: 28
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - D422275

An intermediate in partial synthesis of major human metabolites of Docetaxel (D494420), an antineoplastic.

REFERENCES

• Commercon, A., et al.: Tetrahedron, 50, 10289 (1994)