(2S)-2-{[(tert-butoxy)carbonyl]amino}-3-[4-(prop-2-en-1-yloxy)phenyl]propanoic acid

• ChemBase ID: 139310
• Molecular Formular: C17H23NO5
• Molecular Mass: 321.36822
• Monoisotopic Mass: 321.15762284
• SMILES: CC(C)(C)OC(=O)N[C@@H](Cc1ccc(cc1)OCC=C)C(=O)O
• Canonical SMILES: C=CCOc1ccc(cc1)C[C@@H](C(=O)O)NC(=O)OC(C)(C)C
• InChI: InChI=1S/C17H23NO5/c1-5-10-22-13-8-6-12(7-9-13)11-14(15(19)20)18-16(21)23-17(2,3)4/h5-9,14H,1,10-11H2,2-4H3,(H,18,21)(H,19,20)/t14-/m0/s1
• InChIKey: YIRRNENSHUFZBH-AWEZNQCLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-{[(tert-butoxy)carbonyl]amino}-3-[4-(prop-2-en-1-yloxy)phenyl]propanoic acid
• IUPAC Traditional name: (2S)-2-[(tert-butoxycarbonyl)amino]-3-[4-(prop-2-en-1-yloxy)phenyl]propanoic acid
• Synonyms: Boc-O-allyl-L-tyrosine; Boc-Tyr(Allyl)-OH; N-Boc-O-allyl-L-m-tyrosine; Boc-m-Tyr(Allyl)-OH; 4-Allyloxy-N-Boc-L-phenylalanine; Boc-O-烯丙基-L-酪氨酸; 4-烯丙氧基-N-Boc-L-苯基丙氨酸

Database IDs

• CAS Number: 127132-38-1
• MDL Number: MFCD00273424
• Beilstein Number: 3624582
• PubChem SID: 24887318; 162233558
• PubChem CID: 10853202

CALCULATED PROPERTIES

• Acid pKa: 3.764938
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 1.4072256
• LogD (pH = 7.4): -0.13484305
• Log P: 3.143291
• Molar Refractivity: 85.6152 cm^3
• Polarizability: 33.4591 Å^3
• Polar Surface Area: 84.86 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• German water hazard class: 3
• TSCA Listed: 否
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0% (HPLC); 95%
• Empirical Formula (Hill Notation): C17H23NO5

DETAILS

Sigma Aldrich - 78539

Other Notes
Allyl group side-chain protected tyrosine1; building block for unnatural amino acids by metathesis reaction2
Packaging
5 g in poly bottle