5-(1S,2S,4S,7R,9S,10S,12R,15S)-4,12-bis(acetyloxy)-2-(benzoyloxy)-1-hydroxy-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-15-yl 3-tert-butyl (4S,5R)-2,2-dimethyl-4-phenyl-1,3-oxazolidine-3,5-dicarboxylate

• ChemBase ID: 162490
• Molecular Formular: C51H60Cl3NO17
• Molecular Mass: 1065.3776
• Monoisotopic Mass: 1063.29268251
• SMILES: C12=C([C@H](C[C@](C1(C)C)([C@H](C1[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]1[C@@H](N(C(O1)(C)C)C(=O)OC(C)(C)C)c1ccccc1)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@](C2[C@@H]([C@]2(C(C1=C(C)[C@@H](OC(=O)[C@@H]1OC(N([C@H]1c1ccccc1)C(=O)OC(C)(C)C)(C)C)C2)(C)C)O)OC(=O)c1ccccc1)(CO3)OC(=O)C
• InChI: InChI=1S/C51H60Cl3NO17/c1-26-31(67-42(60)37-35(29-18-14-12-15-19-29)55(47(9,10)71-37)43(61)72-45(4,5)6)23-50(63)40(69-41(59)30-20-16-13-17-21-30)38-48(11,39(58)36(66-27(2)56)34(26)46(50,7)8)32(68-44(62)65-25-51(52,53)54)22-33-49(38,24-64-33)70-28(3)57/h12-21,31-33,35-38,40,63H,22-25H2,1-11H3/t31-,32-,33+,35-,36+,37+,38?,40-,48+,49-,50+/m0/s1
• InChIKey: QTSBQWAZXIXUNK-CAMPFOANSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-(1S,2S,4S,7R,9S,10S,12R,15S)-4,12-bis(acetyloxy)-2-(benzoyloxy)-1-hydroxy-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-15-yl 3-tert-butyl (4S,5R)-2,2-dimethyl-4-phenyl-1,3-oxazolidine-3,5-dicarboxylate
• IUPAC Traditional name: 5-(1S,2S,4S,7R,9S,10S,12R,15S)-4,12-bis(acetyloxy)-2-(benzoyloxy)-1-hydroxy-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-15-yl 3-tert-butyl (4S,5R)-2,2-dimethyl-4-phenyl-1,3-oxazolidine-3,5-dicarboxylate
• Synonyms: 13-{[(3-t-Boc)-2,2-dimethyl-4S-phenyl-1,3-oxazolidin-5R-yl]formyl}-7-O-(2,2,2-trichloroethyl)oxy]carbonyl) Baccatin III; (4S,5R)-2,2-Dimethyl-4-phenyl-3,5-oxazolidinedicarboxylic Acid 5-[(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] 3-(1,1-dimethylethyl) Ester

Database IDs

• CAS Number: 143527-73-5
• PubChem SID: 162256625
• PubChem CID: 46780866

CALCULATED PROPERTIES

• Acid pKa: 11.219194
• H Acceptors: 11
• H Donor: 1
• LogD (pH = 5.5): 7.276462
• LogD (pH = 7.4): 7.276397
• Log P: 7.276463
• Molar Refractivity: 256.1353 cm^3
• Polarizability: 102.22889 Å^3
• Polar Surface Area: 226.03 Å^2
• Rotatable Bonds: 18
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

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

DETAILS

Toronto Research Chemicals - B648475

A precursor to Paclitaxel.