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

• ChemBase ID: 163361
• Molecular Formular: C14H26O4Si
• Molecular Mass: 286.43934
• Monoisotopic Mass: 286.16003584
• SMILES: [C@H]12C[C@H]([C@@H]([C@H]1CC(=O)O2)CO[Si](C(C)(C)C)(C)C)O
• Canonical SMILES: O=C1O[C@@H]2[C@H](C1)[C@H]([C@@H](C2)O)CO[Si](C(C)(C)C)(C)C
• InChI: InChI=1S/C14H26O4Si/c1-14(2,3)19(4,5)17-8-10-9-6-13(16)18-12(9)7-11(10)15/h9-12,15H,6-8H2,1-5H3/t9-,10-,11-,12+/m1/s1
• InChIKey: FFONLBDIZPCEQL-KKOKHZNYSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 65025-94-7
• PubChem SID: 162257496
• PubChem CID: 10613232

CALCULATED PROPERTIES

• Acid pKa: 14.779908
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 1.238
• LogD (pH = 7.4): 1.238
• Log P: 1.238
• Molar Refractivity: 69.6958 cm^3
• Polarizability: 30.101715 Å^3
• Polar Surface Area: 55.76 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

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

DETAILS

Toronto Research Chemicals - B691480

Intermediate in the preparation of prostaglandin derivatives

REFERENCES

• Sugahara, T., et al.: Chem. Pharm. Bull., 39, 2758 (1991)