methyl (5Z)-7-[(1R,2S,3R,5S)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}-5-hydroxy-3-(oxan-2-yloxy)cyclopentyl]hept-5-enoate

• ChemBase ID: 163398
• Molecular Formular: C35H50O6Si
• Molecular Mass: 594.8534
• Monoisotopic Mass: 594.33766585
• SMILES: [C@H]1([C@H]([C@@H](C[C@@H]1O)OC1OCCCC1)CO[Si](C(C)(C)C)(c1ccccc1)c1ccccc1)C/C=C\CCCC(=O)OC
• Canonical SMILES: COC(=O)CCC/C=C\C[C@H]1[C@@H](O)C[C@H]([C@@H]1CO[Si](C(C)(C)C)(c1ccccc1)c1ccccc1)OC1CCCCO1
• InChI: InChI=1S/C35H50O6Si/c1-35(2,3)42(27-17-9-7-10-18-27,28-19-11-8-12-20-28)40-26-30-29(21-13-5-6-14-22-33(37)38-4)31(36)25-32(30)41-34-23-15-16-24-39-34/h5,7-13,17-20,29-32,34,36H,6,14-16,21-26H2,1-4H3/b13-5-/t29-,30-,31+,32-,34?/m1/s1
• InChIKey: NNCUXEYCPYHOSU-ZRLLBJNDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (5Z)-7-[(1R,2S,3R,5S)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}-5-hydroxy-3-(oxan-2-yloxy)cyclopentyl]hept-5-enoate
• IUPAC Traditional name: methyl (5Z)-7-[(1R,2S,3R,5S)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}-5-hydroxy-3-(oxan-2-yloxy)cyclopentyl]hept-5-enoate
• Synonyms: [1R-[1α(Z),2β,3α,5α]]-7-[2-[[[(1,1-Dimethylethyl)diphenylsilyl]oxy]methyl]-5-hydroxy-3-[(tetrahydro-2H-pyran-2-yl)oxy]cyclopentyl]-5-heptenoic Acid Methyl Ester; (1R,2S,3R,5S,δZ)-2-(tert-Butyldiphenylsilyloxy)methyl-5-hydroxy-3-tetrahydropyranyloxy-cyclopentanehept-δ-en-oic Acid Methyl Ester (Mixture of Diastereomers)

Database IDs

• CAS Number: 172016-60-3
• PubChem SID: 162257533
• PubChem CID: 15018467

CALCULATED PROPERTIES

• Acid pKa: 14.838523
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 6.8196
• LogD (pH = 7.4): 6.8196
• Log P: 6.8196
• Molar Refractivity: 164.2518 cm^3
• Polarizability: 66.97018 Å^3
• Polar Surface Area: 74.22 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Acetone; Chloroform; Dichloromethane; Ethyl Acetate; Methanol

DETAILS

Toronto Research Chemicals - B691655

Intermediate in the production of Limaprost.