methyl (2S)-2-{[(benzyloxy)carbonyl]amino}-3-hydroxypropanoate

• ChemBase ID: 148024
• Molecular Formular: C12H15NO5
• Molecular Mass: 253.2512
• Monoisotopic Mass: 253.09502259
• SMILES: COC(=O)[C@H](CO)NC(=O)OCc1ccccc1
• Canonical SMILES: OC[C@@H](C(=O)OC)NC(=O)OCc1ccccc1
• InChI: InChI=1S/C12H15NO5/c1-17-11(15)10(7-14)13-12(16)18-8-9-5-3-2-4-6-9/h2-6,10,14H,7-8H2,1H3,(H,13,16)/t10-/m0/s1
• InChIKey: CINAUOAOVQPWIB-JTQLQIEISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2S)-2-{[(benzyloxy)carbonyl]amino}-3-hydroxypropanoate
• IUPAC Traditional name: methyl (2S)-2-{[(benzyloxy)carbonyl]amino}-3-hydroxypropanoate
• Synonyms: N-Carbobenzoxy-L-serine methyl ester; N-Cbz-L-Serine methyl ester; N-Z-L-serine methyl ester; N-Z-L-丝氨酸甲酯

Database IDs

• CAS Number: 1676-81-9
• MDL Number: MFCD00077039; MFCD00063295
• PubChem SID: 24870568; 162242204
• PubChem CID: 6999535

CALCULATED PROPERTIES

• Polarizability: 24.739225 Å^3
• Polar Surface Area: 84.86 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true
• Acid pKa: 13.012634
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 0.6828836
• LogD (pH = 7.4): 0.68288267
• Log P: 0.6828836
• Molar Refractivity: 62.4901 cm^3

PROPERTIES

Physical Property

• Melting Point: 41-43 °C(lit.)
• Boiling Point: 170 °C/0.01 mmHg(lit.)
• Flash Point: 113 °C; 235 °F

Safety Information

• German water hazard class: 3

Product Information

• Purity: 95%; 95+%
• Linear Formula: HOCH2CH(NHCO2CH2C6H5)CO2CH3

DETAILS

Sigma Aldrich - 469165

Application
This protected serine has been employed as a starting material for the Cbz analog of Garner′s aldehyde,1,2 2,3-diaminopropanol,3 and optically active derivatives of 2-amino-1,3-propanediol.4
Packaging
1, 10 g in glass bottle