1-[(1S,2R,5S,10S,11S,14R,15S)-5-[(tert-butyldimethylsilyl)oxy]-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadec-7-en-14-yl]ethan-1-one

• ChemBase ID: 163378
• Molecular Formular: C27H46O2Si
• Molecular Mass: 430.73844
• Monoisotopic Mass: 430.32670724
• SMILES: [C@@]12(C(=CC[C@@H]3[C@@H]1CC[C@]1([C@H]3CC[C@H]1C(=O)C)C)C[C@H](CC2)O[Si](C(C)(C)C)(C)C)C
• Canonical SMILES: CC(=O)[C@@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CC=C2[C@]1(C)CC[C@@H](C2)O[Si](C(C)(C)C)(C)C
• InChI: InChI=1S/C27H46O2Si/c1-18(28)22-11-12-23-21-10-9-19-17-20(29-30(7,8)25(2,3)4)13-15-26(19,5)24(21)14-16-27(22,23)6/h9,20-24H,10-17H2,1-8H3/t20-,21-,22-,23-,24-,26-,27+/m0/s1
• InChIKey: XMTKPEYPGQAHCU-OZESZIMSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(1S,2R,5S,10S,11S,14R,15S)-5-[(tert-butyldimethylsilyl)oxy]-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-7-en-14-yl]ethan-1-one
• IUPAC Traditional name: 1-[(1S,2R,5S,10S,11S,14R,15S)-5-[(tert-butyldimethylsilyl)oxy]-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-7-en-14-yl]ethanone
• Synonyms: 3β-(tert-Butyldimethylsiloxy)pregn-5-en-20-one; (3β)-3-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]pregn-5-en-20-one; 3-tert-Butyldimethylsilyloxy Pregnenolone

Database IDs

• CAS Number: 58701-45-4
• PubChem SID: 162257513
• PubChem CID: 13845368

CALCULATED PROPERTIES

• Acid pKa: 19.403038
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 6.6419
• LogD (pH = 7.4): 6.6419
• Log P: 6.6419
• Molar Refractivity: 123.6048 cm^3
• Polarizability: 51.012783 Å^3
• Polar Surface Area: 26.3 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate

DETAILS

Toronto Research Chemicals - B691555

Protected Pregnenolone derivative.

REFERENCES

• Kim, B., et al.: Bioorg. Med. Chem. Lett., 10, 357 (2000)
• Watanabe, B., et al.: Steroids, 69, 483 (2000)