benzyl N-[(2S)-1-hydroxy-3-phenylpropan-2-yl]carbamate

• ChemBase ID: 147920
• Molecular Formular: C17H19NO3
• Molecular Mass: 285.33766
• Monoisotopic Mass: 285.13649347
• SMILES: c1ccc(cc1)C[C@@H](CO)NC(=O)OCc1ccccc1
• Canonical SMILES: OC[C@H](Cc1ccccc1)NC(=O)OCc1ccccc1
• InChI: InChI=1S/C17H19NO3/c19-12-16(11-14-7-3-1-4-8-14)18-17(20)21-13-15-9-5-2-6-10-15/h1-10,16,19H,11-13H2,(H,18,20)/t16-/m0/s1
• InChIKey: WPOFMMJJCPZPAO-INIZCTEOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: benzyl N-[(2S)-1-hydroxy-3-phenylpropan-2-yl]carbamate
• IUPAC Traditional name: benzyl N-[(2S)-1-hydroxy-3-phenylpropan-2-yl]carbamate
• Synonyms: (S)-(-)-2-(Carbobenzyloxyamino)-3-phenyl-1-propanol; (S)-2-(Z-Amino)-3-phenyl-1-propanol; N-(Carbobenzyloxy)-L-phenylalaninol; Z-L-Phenylalaninol; (S)-2-Carbobenzyloxyamino-3-phenyl-1-propanol; N-Cbz-L-phenylalaninol; N-Benzyloxycarbonyl-L-phenylalaninol; (S)-2-(Z-氨基)-3-苯基-1-丙醇; (S)-(-)-2-(苄氧羰基氨基)-3-苯基-1-丙醇; N-(苄氧羰基)-L-苯丙氨醇; Z-L-苯丙氨醇; N-苄氧羰基-L-苯氨基丙醇

Database IDs

• CAS Number: 6372-14-1
• MDL Number: MFCD00191138
• Beilstein Number: 2816420
• PubChem SID: 162242101; 24866399; 24890380
• PubChem CID: 853481

CALCULATED PROPERTIES

• Acid pKa: 14.242312
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 2.9199514
• LogD (pH = 7.4): 2.9199512
• Log P: 2.9199514
• Molar Refractivity: 80.9289 cm^3
• Polarizability: 31.6439 Å^3
• Polar Surface Area: 58.56 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 90-92 °C(lit.); 92-95 °C; 92-95°C
• Optical Rotation: [α]20/D -30°, c = 1 in chloroform; [α]20/D -43±1°, c = 2% in methanol

Safety Information

• German water hazard class: 3
• TSCA Listed: 否
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥98.5% (sum of enantiomers, HPLC); 97%; 98%
• Grade: puriss.
• Linear Formula: C6H5CH2CH(NHCO2CH2C6H5)CH2OH
• Empirical Formula (Hill Notation): C17H19NO3

DETAILS

Sigma Aldrich - 421723

Application
Employed in the synthesis of biochemically active compounds.1 Building block for the synthesis of HIV protease inhibitors.2,3,4,5,6,7
Packaging
5 g in glass bottle

Sigma Aldrich - 97027

Other Notes
Chiral building block; oxidation to the unstable aldehyde1,2