(3aR,4S,5R,6aS)-4-{[(tert-butyldiphenylsilyl)oxy]methyl}-5-hydroxy-hexahydro-2H-cyclopenta[b]furan-2-one

• ChemBase ID: 163401
• Molecular Formular: C24H30O4Si
• Molecular Mass: 410.5781
• Monoisotopic Mass: 410.19133597
• SMILES: [C@H]12C[C@H]([C@@H]([C@H]1CC(=O)O2)CO[Si](C(C)(C)C)(c1ccccc1)c1ccccc1)O
• Canonical SMILES: O=C1O[C@@H]2[C@H](C1)[C@H]([C@@H](C2)O)CO[Si](C(C)(C)C)(c1ccccc1)c1ccccc1
• InChI: InChI=1S/C24H30O4Si/c1-24(2,3)29(17-10-6-4-7-11-17,18-12-8-5-9-13-18)27-16-20-19-14-23(26)28-22(19)15-21(20)25/h4-13,19-22,25H,14-16H2,1-3H3/t19-,20-,21-,22+/m1/s1
• InChIKey: JFKQASGNSCLFLO-YSFYHYPLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3aR,4S,5R,6aS)-4-{[(tert-butyldiphenylsilyl)oxy]methyl}-5-hydroxy-hexahydro-2H-cyclopenta[b]furan-2-one
• IUPAC Traditional name: (3aR,4S,5R,6aS)-4-{[(tert-butyldiphenylsilyl)oxy]methyl}-5-hydroxy-hexahydrocyclopenta[b]furan-2-one
• Synonyms: (3aR,4S,5R,6aS)-4-[[[(1,1-Dimethylethyl)diphenylsilyl]oxy]methyl]hexahydro-5-hydroxy-2H-cyclopenta[b]furan-2-one; (3aR,4S,5R,6aS)-4-(tert-Butyldiphenylsilyloxy)methyl-5-hydroxy-hexahydro-2H-cyclopenta[b]furan-2-one

Database IDs

• CAS Number: 84786-80-1
• PubChem SID: 162257536
• PubChem CID: 10982473

CALCULATED PROPERTIES

• Acid pKa: 14.779866
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 4.3902
• LogD (pH = 7.4): 4.3902
• Log P: 4.3902
• Molar Refractivity: 109.0842 cm^3
• Polarizability: 45.56753 Å^3
• Polar Surface Area: 55.76 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

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

DETAILS

Toronto Research Chemicals - B691670

Intermediate in the preparation of prostaglandin derivatives

REFERENCES

• Klar, U., et al.: Bioorg. Med. Chem. Lett., 5, 1219 (1995)
• Sato, Y., et al.: Chem. Pharm. Bull., 48, 1753 (1995)