(2S,3R)-3-(2H-1,3-benzodioxol-5-yl)-2-{[(benzyloxy)carbonyl]amino}-3-hydroxypropanoic acid

• ChemBase ID: 161702
• Molecular Formular: C18H17NO7
• Molecular Mass: 359.33008
• Monoisotopic Mass: 359.10050189
• SMILES: c12c(ccc(c1)[C@H]([C@H](NC(=O)OCc1ccccc1)C(=O)O)O)OCO2
• Canonical SMILES: O=C(N[C@@H]([C@@H](c1ccc2c(c1)OCO2)O)C(=O)O)OCc1ccccc1
• InChI: InChI=1S/C18H17NO7/c20-16(12-6-7-13-14(8-12)26-10-25-13)15(17(21)22)19-18(23)24-9-11-4-2-1-3-5-11/h1-8,15-16,20H,9-10H2,(H,19,23)(H,21,22)/t15-,16+/m0/s1
• InChIKey: PHFXRWNRHDASFI-JKSUJKDBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R)-3-(2H-1,3-benzodioxol-5-yl)-2-{[(benzyloxy)carbonyl]amino}-3-hydroxypropanoic acid
• IUPAC Traditional name: (2S,3R)-3-(2H-1,3-benzodioxol-5-yl)-2-{[(benzyloxy)carbonyl]amino}-3-hydroxypropanoic acid
• Synonyms: (R,S)-rel-α-Amino-N-benzyloxycarbonyl-β-hydroxy-1,3-benzodioxole-5-propanoic Acid; N-Benzyloxycarbonyl DL-threo-β-(3,4-Methylenedioxyphenyl)serine

Database IDs

• PubChem SID: 162255837
• PubChem CID: 13291946

CALCULATED PROPERTIES

• Acid pKa: 3.2544339
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -0.28154278
• LogD (pH = 7.4): -1.490898
• Log P: 1.9444633
• Molar Refractivity: 87.7707 cm^3
• Polarizability: 34.72815 Å^3
• Polar Surface Area: 114.32 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - B285903

Intermediate in the preparation of DL-threo-Droxidopa, an antiparkinsonian.