methyl (2S,3S,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-{4-[cyano(1-hydroxycyclohexyl)methyl]phenoxy}oxane-2-carboxylate

• ChemBase ID: 170642
• Molecular Formular: C27H33NO11
• Molecular Mass: 547.55102
• Monoisotopic Mass: 547.20536088
• SMILES: c1cc(ccc1C(C1(CCCCC1)O)C#N)O[C@@H]1O[C@H]([C@@H](OC(=O)C)[C@H](OC(=O)C)[C@@H]1OC(=O)C)C(=O)OC
• Canonical SMILES: COC(=O)[C@@H]1O[C@@H](Oc2ccc(cc2)C(C2(O)CCCCC2)C#N)[C@H]([C@H]([C@@H]1OC(=O)C)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C27H33NO11/c1-15(29)35-21-22(36-16(2)30)24(37-17(3)31)26(39-23(21)25(32)34-4)38-19-10-8-18(9-11-19)20(14-28)27(33)12-6-5-7-13-27/h8-11,20-24,26,33H,5-7,12-13H2,1-4H3/t20?,21-,22-,23-,24+,26+/m0/s1
• InChIKey: NYWMHDNYLGDOGH-APEDDKMTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2S,3S,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-{4-[cyano(1-hydroxycyclohexyl)methyl]phenoxy}oxane-2-carboxylate
• IUPAC Traditional name: methyl (2S,3S,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-{4-[cyano(1-hydroxycyclohexyl)methyl]phenoxy}oxane-2-carboxylate
• Synonyms: 4-Hydroxy-α-(1-hydroxycyclohexyl)benzeneacetonitrile 2,3,4-Tri-O-acetyl-β-D-glucuronide Methyl Ester

Database IDs

• PubChem SID: 164226552
• PubChem CID: 71749067

CALCULATED PROPERTIES

• Acid pKa: 13.01249
• H Acceptors: 8
• H Donor: 1
• LogD (pH = 5.5): 1.8721087
• LogD (pH = 7.4): 1.8721077
• Log P: 1.8721087
• Molar Refractivity: 129.8142 cm^3
• Polarizability: 52.66285 Å^3
• Polar Surface Area: 167.68 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Dichloromethane
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - H942865

Intermediate for the synthesis of O-desmethylvenlafaxine Glucuronide.