(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetyloxy)-15-{[(2R,3S)-3-(5,5-dimethyl-2,4-dioxo-1,3-oxazolidin-3-yl)-2-hydroxy-3-phenylpropanoyl]oxy}-1-hydroxy-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: 165487
• Molecular Formular: C49H51Cl6NO19
• Molecular Mass: 1170.64254
• Monoisotopic Mass: 1167.1186445
• SMILES: C1(=C2C([C@@](C[C@@H]1OC(=O)[C@@H]([C@H](c1ccccc1)N1C(=O)C(OC1=O)(C)C)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: O=C(O[C@H]1C(=O)[C@]2(C)[C@@H](OC(=O)OCC(Cl)(Cl)Cl)C[C@@H]3[C@]([C@H]2[C@@H]([C@]2(C(C1=C(C)[C@@H](OC(=O)[C@@H]([C@@H](N1C(=O)OC(C1=O)(C)C)c1ccccc1)O)C2)(C)C)O)OC(=O)c1ccccc1)(CO3)OC(=O)C)OCC(Cl)(Cl)Cl
• InChI: InChI=1S/C49H51Cl6NO19/c1-23-27(70-38(61)32(58)31(25-14-10-8-11-15-25)56-39(62)44(5,6)75-40(56)63)19-47(66)36(73-37(60)26-16-12-9-13-17-26)34-45(7,35(59)33(30(23)43(47,3)4)72-42(65)69-22-49(53,54)55)28(71-41(64)68-21-48(50,51)52)18-29-46(34,20-67-29)74-24(2)57/h8-17,27-29,31-34,36,58,66H,18-22H2,1-7H3/t27-,28-,29+,31-,32+,33+,34-,36-,45+,46-,47+/m0/s1
• InChIKey: VRSGCJUFENMYHX-JMVOMOTHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetyloxy)-15-{[(2R,3S)-3-(5,5-dimethyl-2,4-dioxo-1,3-oxazolidin-3-yl)-2-hydroxy-3-phenylpropanoyl]oxy}-1-hydroxy-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)-15-{[(2R,3S)-3-(5,5-dimethyl-2,4-dioxo-1,3-oxazolidin-3-yl)-2-hydroxy-3-phenylpropanoyl]oxy}-1-hydroxy-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-5,5-dimethyl-2,4-dioxo-β-phenyl-3-Oxazolidinepropanoic 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; 3'-De-tert-butoxycarbonylamino-3'-[3-(5,5-dimethyl-2,4-dioxo-1,3-oxazolidinyl)]-7,10-O-bis{[(2,2,2-trichloroethyl)oxy]carbonyl} Docetaxel

Database IDs

• CAS Number: 160651-94-5
• PubChem SID: 162259620
• PubChem CID: 15765792

CALCULATED PROPERTIES

• Acid pKa: 11.955903
• H Acceptors: 13
• H Donor: 2
• LogD (pH = 5.5): 7.8254437
• LogD (pH = 7.4): 7.825432
• Log P: 7.8254437
• Molar Refractivity: 263.7693 cm^3
• Polarizability: 105.17846 Å^3
• Polar Surface Area: 263.33 Å^2
• Rotatable Bonds: 21
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate; Methanol

DETAILS

Toronto Research Chemicals - D209700

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

REFERENCES

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