(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetyloxy)-1-hydroxy-15-{[(2R,3S)-2-hydroxy-3-phenyl-3-[(2H5)phenylformamido]propanoyl]oxy}-10,14,17,17-tetramethyl-11-oxo-9-{[(2,2,2-trichloroethoxy)carbonyl]oxy}-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl benzoate

• ChemBase ID: 178955
• Molecular Formular: C50H52Cl3NO16
• Molecular Mass: 1029.30398
• Monoisotopic Mass: 1027.23516763
• SMILES: C12=C([C@H](C[C@](C1(C)C)([C@H]([C@H]1[C@](C(=O)[C@@H]2OC(=O)C)([C@H](C[C@@H]2[C@]1(CO2)OC(=O)C)OC(=O)OCC(Cl)(Cl)Cl)C)OC(=O)c1ccccc1)O)OC(=O)[C@@H]([C@H](c1ccccc1)NC(=O)c1ccccc1)O)C
• Canonical SMILES: CC(=O)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](c1ccccc1)NC(=O)c1ccccc1)O)C2)(C)C)O)OC(=O)c1ccccc1)(CO3)OC(=O)C
• InChI: InChI=1S/C50H52Cl3NO16/c1-26-32(67-44(61)37(57)36(29-16-10-7-11-17-29)54-42(59)30-18-12-8-13-19-30)23-49(63)41(69-43(60)31-20-14-9-15-21-31)39-47(6,40(58)38(66-27(2)55)35(26)46(49,4)5)33(68-45(62)65-25-50(51,52)53)22-34-48(39,24-64-34)70-28(3)56/h7-21,32-34,36-39,41,57,63H,22-25H2,1-6H3,(H,54,59)/t32-,33-,34+,36-,37+,38+,39-,41-,47+,48-,49+/m0/s1
• InChIKey: ARZHVJDHKCYODM-MUQZGBOESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetyloxy)-1-hydroxy-15-{[(2R,3S)-2-hydroxy-3-phenyl-3-[(^2H₅)phenylformamido]propanoyl]oxy}-10,14,17,17-tetramethyl-11-oxo-9-{[(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)-4,12-bis(acetyloxy)-1-hydroxy-15-{[(2R,3S)-2-hydroxy-3-phenyl-3-[(^2H₅)phenylformamido]propanoyl]oxy}-10,14,17,17-tetramethyl-11-oxo-9-{[(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: (αR,βS)-β-(Benzoylamino)-α-hydroxybenzenepropanoic acid, , (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-6,12b-Bis(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-[[(2,2,2-trichloroethoxy)carbonyl]oxy]-7,11-methano-1H-cyclodeca[3,4]benz[1,2-b]oxet-9-yl Ester-d5; 7-(2,2,2-Trichloroethyloxycarbonyl)taxol-d5; 7-{[(2,2,2,-Trichloroethyl)oxy]carbonyl} Paclitaxel-d5

Database IDs

• PubChem SID: 164234865
• PubChem CID: 71752704

CALCULATED PROPERTIES

• Acid pKa: 11.152603
• H Acceptors: 11
• H Donor: 3
• LogD (pH = 5.5): 6.1744113
• LogD (pH = 7.4): 6.174336
• Log P: 6.1744127
• Molar Refractivity: 249.0241 cm^3
• Polarizability: 98.658226 Å^3
• Polar Surface Area: 236.59 Å^2
• Rotatable Bonds: 19
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate
• Apperance: Off-White Powder

DETAILS

Toronto Research Chemicals - T774147

Labelled 7-{[(2,2,2,-Trichloroethyl)oxy]carbonyl} Paclitaxel is used in the semi-synthesis of Taxol (P132500) and Docetaxel (D494420).

REFERENCES

• Commercon, A., et al.: Tetrahedr. Lett., 33, 5185 (1992)