methyl (2S)-3-[4-(benzyloxy)-3-hydroxyphenyl]-2-{[(benzyloxy)carbonyl]amino}propanoate

• ChemBase ID: 161427
• Molecular Formular: C25H25NO6
• Molecular Mass: 435.4691
• Monoisotopic Mass: 435.16818753
• SMILES: c1c(c(ccc1C[C@H](NC(=O)OCc1ccccc1)C(=O)OC)OCc1ccccc1)O
• Canonical SMILES: COC(=O)[C@H](Cc1ccc(c(c1)O)OCc1ccccc1)NC(=O)OCc1ccccc1
• InChI: InChI=1S/C25H25NO6/c1-30-24(28)21(26-25(29)32-17-19-10-6-3-7-11-19)14-20-12-13-23(22(27)15-20)31-16-18-8-4-2-5-9-18/h2-13,15,21,27H,14,16-17H2,1H3,(H,26,29)/t21-/m0/s1
• InChIKey: XRUVERDUHRJKJQ-NRFANRHFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2S)-3-[4-(benzyloxy)-3-hydroxyphenyl]-2-{[(benzyloxy)carbonyl]amino}propanoate
• IUPAC Traditional name: methyl (2S)-3-[4-(benzyloxy)-3-hydroxyphenyl]-2-{[(benzyloxy)carbonyl]amino}propanoate
• Synonyms: 3-Hydroxy-N-[(phenylmethoxy)carbonyl]-O-(phenylmethyl)-L-tyrosine Methyl Ester; 4-O-Benzyl-N-[(benzyloxy)carbonyl]-L-DOPA Methyl Ester

Database IDs

• CAS Number: 105229-41-2
• PubChem SID: 162255562
• PubChem CID: 11316490

CALCULATED PROPERTIES

• Acid pKa: 9.86373
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 4.649338
• LogD (pH = 7.4): 4.6478763
• Log P: 4.6493564
• Molar Refractivity: 118.6221 cm^3
• Polarizability: 46.351063 Å^3
• Polar Surface Area: 94.09 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane
• Apperance: Yellow Sticky Oil

DETAILS

Toronto Research Chemicals - B232890

Intermediate in the preparation of a L-DOPA (D533751) metabolite.