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

• ChemBase ID: 159174
• Molecular Formular: C27H27NO6
• Molecular Mass: 461.50638
• Monoisotopic Mass: 461.18383759
• SMILES: c1c(c(ccc1C[C@H](NC(=O)OCc1ccccc1)C(=O)OC)OCc1ccccc1)C(=O)C
• Canonical SMILES: COC(=O)[C@H](Cc1ccc(c(c1)C(=O)C)OCc1ccccc1)NC(=O)OCc1ccccc1
• InChI: InChI=1S/C27H27NO6/c1-19(29)23-15-22(13-14-25(23)33-17-20-9-5-3-6-10-20)16-24(26(30)32-2)28-27(31)34-18-21-11-7-4-8-12-21/h3-15,24H,16-18H2,1-2H3,(H,28,31)/t24-/m0/s1
• InChIKey: JZMQRDHUCGTNDC-DEOSSOPVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2S)-3-[3-acetyl-4-(benzyloxy)phenyl]-2-{[(benzyloxy)carbonyl]amino}propanoate
• IUPAC Traditional name: methyl (2S)-3-[3-acetyl-4-(benzyloxy)phenyl]-2-{[(benzyloxy)carbonyl]amino}propanoate
• Synonyms: 3-Acetyl-N-[(phenylmethoxy)carbonyl]-O-(phenylmethyl)-L-tyrosine Methyl Ester; 3-Acetyl-N-benzyloxycarbonyl-4-O-benzyl-L-tyrosine Methyl Ester

Database IDs

• CAS Number: 105205-69-4
• PubChem SID: 162253309
• PubChem CID: 13919754

CALCULATED PROPERTIES

• Acid pKa: 12.94741
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 4.510569
• LogD (pH = 7.4): 4.510568
• Log P: 4.5105696
• Molar Refractivity: 127.044 cm^3
• Polarizability: 49.478794 Å^3
• Polar Surface Area: 90.93 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane
• Apperance: Pale Yellow Solid

DETAILS

Toronto Research Chemicals - A171020

Protected L-DOPA (D533751) derivative.

REFERENCES

• Boger, D. & Yohannes, D.; J. Org. Chem. 52, 5283 (1987)