(2S)-2-{[(tert-butoxy)carbonyl]amino}-5-(cyclohexyloxy)-5-oxopentanoic acid

• ChemBase ID: 106102
• Molecular Formular: C16H27NO6
• Molecular Mass: 329.38868
• Monoisotopic Mass: 329.18383759
• SMILES: CC(C)(C)OC(=O)N[C@@H](CCC(=O)OC1CCCCC1)C(=O)O
• Canonical SMILES: O=C(OC1CCCCC1)CC[C@@H](C(=O)O)NC(=O)OC(C)(C)C
• InChI: InChI=1S/C16H27NO6/c1-16(2,3)23-15(21)17-12(14(19)20)9-10-13(18)22-11-7-5-4-6-8-11/h11-12H,4-10H2,1-3H3,(H,17,21)(H,19,20)/t12-/m0/s1
• InChIKey: FDNMLANBNJDIRG-LBPRGKRZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-{[(tert-butoxy)carbonyl]amino}-5-(cyclohexyloxy)-5-oxopentanoic acid
• IUPAC Traditional name: (2S)-2-[(tert-butoxycarbonyl)amino]-5-(cyclohexyloxy)-5-oxopentanoic acid
• Synonyms: N-α-t-BOC-L-GLUTAMIC ACID γ-CYCLOHEXYL ESTER; Boc-Glu(OcHx)-OH; Boc-L-glutamic acid γ-cyclohexyl ester; Boc-L-glutamic acid 5-cyclohexyl ester; Boc-L-谷氨酸-γ-环己酯; Boc-L-谷氨酸-5-环己酯

Database IDs

• CAS Number: 73821-97-3
• MDL Number: MFCD00065570
• Beilstein Number: 3595818
• PubChem SID: 162087276; 24849433
• PubChem CID: 7017890

CALCULATED PROPERTIES

• Acid pKa: 3.8731062
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 0.8737729
• LogD (pH = 7.4): -0.72187793
• Log P: 2.5054
• Molar Refractivity: 81.944 cm^3
• Polarizability: 32.761013 Å^3
• Polar Surface Area: 101.93 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 54-57 °C
• Optical Rotation: [α]20/D -16.5±1°, c = 2% in DMF

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0% (sum of enantiomers, TLC)
• Grade: purum
• Impurities: ≤5% solvent
• Linear Formula: C6H11OCOCH2CH2CH(COOH)NHCOOC(CH3)3

DETAILS

MP Biomedicals - 02199062

Side chain protecting group for glutamic acid.
Minimizes side reactions during basic and acid treatments.

REFERENCES

• J.P. Tam, et al. Tetrahedron Lett., 42: 4033, (1979).