(3R,4S)-4-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-1-hydroxy-2,2,6,6-tetramethylpiperidine-3-carboxylic acid

• ChemBase ID: 169489
• Molecular Formular: C25H30N2O5
• Molecular Mass: 438.5161
• Monoisotopic Mass: 438.21547207
• SMILES: N1(C(C[C@@H]([C@H](C1(C)C)C(=O)O)NC(=O)OCC1c2c(c3c1cccc3)cccc2)(C)C)O
• Canonical SMILES: O=C(N[C@H]1CC(C)(C)N(C([C@@H]1C(=O)O)(C)C)O)OCC1c2ccccc2c2c1cccc2
• InChI: InChI=1S/C25H30N2O5/c1-24(2)13-20(21(22(28)29)25(3,4)27(24)31)26-23(30)32-14-19-17-11-7-5-9-15(17)16-10-6-8-12-18(16)19/h5-12,19-21,31H,13-14H2,1-4H3,(H,26,30)(H,28,29)/t20-,21-/m0/s1
• InChIKey: FEDYWNJTEUNDMB-SFTDATJTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,4S)-4-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-1-hydroxy-2,2,6,6-tetramethylpiperidine-3-carboxylic acid
• IUPAC Traditional name: (3R,4S)-4-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-1-hydroxy-2,2,6,6-tetramethylpiperidine-3-carboxylic acid
• Synonyms: (3S,4S)-3-Carboxy-4-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-2,2,6,6-tetramethyl-1-piperidinyloxy; Fmoc-(3S,4S)-4-amino-1-oxyl-2,2,6,6-tetramethylpiperidine-3-carboxylic Acid

Database IDs

• CAS Number: 583827-12-7
• PubChem SID: 162263621
• PubChem CID: 71317002

CALCULATED PROPERTIES

• Acid pKa: 4.3086214
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 2.0402722
• LogD (pH = 7.4): 0.3014858
• Log P: 3.2621367
• Molar Refractivity: 120.0091 cm^3
• Polarizability: 48.303413 Å^3
• Polar Surface Area: 99.1 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - F860860

A protected spin-labelled, cyclic, chiral β-amino acid resolved in an enantiomerically pure state.

REFERENCES

• Wright, K., et al.: Tetrahedron Letters, 44, 3381 (2003)