methyl (2S,3S,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-(4-formyl-2-methoxyphenoxy)oxane-2-carboxylate

• ChemBase ID: 169418
• Molecular Formular: C21H24O12
• Molecular Mass: 468.40806
• Monoisotopic Mass: 468.12677621
• SMILES: c1(c(ccc(c1)C=O)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1OC(=O)C)OC(=O)C)OC(=O)C)C(=O)OC)OC
• Canonical SMILES: COC(=O)[C@@H]1O[C@@H](Oc2ccc(cc2OC)C=O)[C@H]([C@H]([C@@H]1OC(=O)C)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C21H24O12/c1-10(23)29-16-17(30-11(2)24)19(31-12(3)25)21(33-18(16)20(26)28-5)32-14-7-6-13(9-22)8-15(14)27-4/h6-9,16-19,21H,1-5H3/t16-,17-,18-,19+,21+/m0/s1
• InChIKey: QTHPZBHVIGLWPP-VDRZXAFZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2S,3S,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-(4-formyl-2-methoxyphenoxy)oxane-2-carboxylate
• IUPAC Traditional name: methyl (2S,3S,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-(4-formyl-2-methoxyphenoxy)oxane-2-carboxylate
• Synonyms: 4-Formyl-2-methoxyphenyl β-D-Glucopyranosiduronic Acid Triacetate Methyl Ester

Database IDs

• CAS Number: 704885-44-9
• PubChem SID: 162263550
• PubChem CID: 71316957

CALCULATED PROPERTIES

• H Acceptors: 8
• H Donor: 0
• LogD (pH = 5.5): 0.7459883
• LogD (pH = 7.4): 0.7459883
• Log P: 0.7459883
• Molar Refractivity: 105.3215 cm^3
• Polarizability: 42.730946 Å^3
• Polar Surface Area: 149.96 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; Chloroform; Dichloromethane; Dimethyl Formamide; Ethyl Acetate; Methanol
• Apperance: Off-White Solid

DETAILS

Toronto Research Chemicals - F700790

Used in the preparation of epothilone-saccharide conjugates for the treatment of proliferative diseases.