tert-butyl N-[(2S)-1-hydroxy-4-methylpentan-2-yl]carbamate

• ChemBase ID: 90711
• Molecular Formular: C11H23NO3
• Molecular Mass: 217.30522
• Monoisotopic Mass: 217.1677936
• SMILES: OC[C@@H](NC(=O)OC(C)(C)C)CC(C)C
• Canonical SMILES: OC[C@@H](NC(=O)OC(C)(C)C)CC(C)C
• InChI: InChI=1S/C11H23NO3/c1-8(2)6-9(7-13)12-10(14)15-11(3,4)5/h8-9,13H,6-7H2,1-5H3,(H,12,14)/t9-/m0/s1
• InChIKey: LQTMEOSBXTVYRM-VIFPVBQESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: tert-butyl N-[(2S)-1-hydroxy-4-methylpentan-2-yl]carbamate
• IUPAC Traditional name: tert-butyl N-[(2S)-1-hydroxy-4-methylpentan-2-yl]carbamate
• Synonyms: Boc-L-leucinol; (2S)-2-Amino-4-methylpentan-1-ol, N-BOC protected; L-Leucinol, N-BOC protected; tert-Butyl [(2S)-1-hydroxy-4-methylpent-2-yl]carbamate; Boc-(2S)-amino-4-methyl-1-pentanol; N-(tert-Butoxycarbonyl)-L-leucinol; N-Boc-L-leucinol; N-Boc-L-Leucinol; Boc-L-亮氨醇; N-Boc-L-亮氨醇

Database IDs

• CAS Number: 82010-31-9
• MDL Number: MFCD00076950
• Beilstein Number: 4178460
• PubChem SID: 162077455; 24849316; 24867337
• PubChem CID: 7018766

CALCULATED PROPERTIES

• Acid pKa: 14.568467
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 1.8472217
• LogD (pH = 7.4): 1.8472216
• Log P: 1.8472217
• Molar Refractivity: 59.1765 cm^3
• Polarizability: 23.525078 Å^3
• Polar Surface Area: 58.56 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 212-214°C; 212-214°C
• Flash Point: >110 °C; >110°C; >110°C(230°F); >230 °F
• Density: 0.98; 0.980
• Refractive Index: 1.4500; n20/D 1.450
• Optical Rotation: [α]20/D -27.5±1°, c = 2% in methanol; [α]23/D -27°, c = 2 in methanol; -27.5 (c=2 in methanol)

Safety Information

• Storage Warning: Irritant/Store under Argon
• German water hazard class: 3
• TSCA Listed: 否
• Personal Protective Equipment: Eyeshields, Gloves

Product Information

• Purity: ≥97.0% (GC); 95%; 97%
• Grade: purum
• Linear Formula: (CH3)2CHCH2CH[NHCO2C(CH3)3]CH2OH

DETAILS

Sigma Aldrich - 441198

Application
Precursor to enantiomerically pure α-methyl amines.1 Starting material for the synthesis of enantiopure homo-β-amino acids2,3 and N-protected α-amino aldehydes.4 Used in the total synthesis of the gastro-protective amicoumacin C.5
Packaging
1, 5 g in glass bottle

Sigma Aldrich - 15494

Other Notes
Chiral building block; preparation of the unstable aldehyde1,2