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

• ChemBase ID: 152533
• Molecular Formular: C15H23NO5S
• Molecular Mass: 329.41182
• Monoisotopic Mass: 329.12969384
• SMILES: Cc1ccc(cc1)S(=O)(=O)O.CC(C)[C@@H](C(=O)OCC=C)N
• Canonical SMILES: Cc1ccc(cc1)S(=O)(=O)O.C=CCOC(=O)[C@H](C(C)C)N
• InChI: InChI=1S/C8H15NO2.C7H8O3S/c1-4-5-11-8(10)7(9)6(2)3;1-6-2-4-7(5-3-6)11(8,9)10/h4,6-7H,1,5,9H2,2-3H3;2-5H,1H3,(H,8,9,10)/t7-;/m0./s1
• InChIKey: HSIRKDASFUCGOZ-FJXQXJEOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-methylbenzene-1-sulfonic acid prop-2-en-1-yl (2S)-2-amino-3-methylbutanoate
• IUPAC Traditional name: toluenesulfonic acid prop-2-en-1-yl (2S)-2-amino-3-methylbutanoate
• Synonyms: L-Valine allyl ester p-toluenesulfonate salt; L-缬氨酸烯丙基酯 对甲苯磺酸盐

Database IDs

• CAS Number: 88224-02-6
• MDL Number: MFCD00077953
• Beilstein Number: 5200860
• PubChem SID: 162246678; 24890033
• PubChem CID: 71311559

CALCULATED PROPERTIES

• Acid pKa: -2.1372879
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -0.7088225
• LogD (pH = 7.4): -0.7088248
• Log P: 1.6675739
• Molar Refractivity: 41.7217 cm^3
• Polarizability: 16.707253 Å^3
• Polar Surface Area: 54.37 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 117-120 °C
• Optical Rotation: [α]20/D +5.5±1°, c = 1% in methanol

Safety Information

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

Product Information

• Purity: ≥99.0%
• Linear Formula: (CH3)2CHCH(NH2)COOCH2CH=CH2 · C7H8O3S

DETAILS

Sigma Aldrich - 94645

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