4-methylbenzene-1-sulfonic acid prop-2-en-1-yl (2S)-2-amino-3-phenylpropanoate

• ChemBase ID: 139201
• Molecular Formular: C19H23NO5S
• Molecular Mass: 377.45462
• Monoisotopic Mass: 377.12969384
• SMILES: Cc1ccc(cc1)S(=O)(=O)O.C=CCOC(=O)[C@H](Cc1ccccc1)N
• Canonical SMILES: Cc1ccc(cc1)S(=O)(=O)O.C=CCOC(=O)[C@H](Cc1ccccc1)N
• InChI: InChI=1S/C12H15NO2.C7H8O3S/c1-2-8-15-12(14)11(13)9-10-6-4-3-5-7-10;1-6-2-4-7(5-3-6)11(8,9)10/h2-7,11H,1,8-9,13H2;2-5H,1H3,(H,8,9,10)/t11-;/m0./s1
• InChIKey: PKXPRZFLCJFMHN-MERQFXBCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-methylbenzene-1-sulfonic acid prop-2-en-1-yl (2S)-2-amino-3-phenylpropanoate
• IUPAC Traditional name: toluenesulfonic acid prop-2-en-1-yl (2S)-2-amino-3-phenylpropanoate
• Synonyms: L-Phenylalanine allyl ester p-toluenesulfonate salt; L-苯丙氨酸烯丙酯 对甲苯磺酸盐

Database IDs

• CAS Number: 88224-00-4
• MDL Number: MFCD00043306
• Beilstein Number: 5212778
• PubChem SID: 24887250; 162233449
• PubChem CID: 45072173

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 0.48615032
• LogD (pH = 7.4): 1.8188899
• Log P: 1.9547589
• Molar Refractivity: 59.0481 cm^3
• Polarizability: 23.429575 Å^3
• Polar Surface Area: 52.32 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 155-158 °C
• Optical Rotation: [α]20/D +10.5±1°, c = 1% in DMF

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Empirical Formula (Hill Notation): C12H15NO2 · C7H8O3S

DETAILS

Sigma Aldrich - 78055

Other Notes
Used in peptide and N-glycopeptide synthesis; the ester is selectively deblocked with (Ph3P)3RhCl1