ethyl (2S)-2-{[(tert-butoxy)carbonyl]amino}-4-[(4-methylbenzenesulfonyl)oxy]butanoate

• ChemBase ID: 162590
• Molecular Formular: C18H27NO7S
• Molecular Mass: 401.47448
• Monoisotopic Mass: 401.15082321
• SMILES: C([C@@H](C(=O)OCC)NC(=O)OC(C)(C)C)COS(=O)(=O)c1ccc(cc1)C
• Canonical SMILES: CCOC(=O)[C@@H](NC(=O)OC(C)(C)C)CCOS(=O)(=O)c1ccc(cc1)C
• InChI: InChI=1S/C18H27NO7S/c1-6-24-16(20)15(19-17(21)26-18(3,4)5)11-12-25-27(22,23)14-9-7-13(2)8-10-14/h7-10,15H,6,11-12H2,1-5H3,(H,19,21)/t15-/m0/s1
• InChIKey: JIEKUIWRCLMXBI-HNNXBMFYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl (2S)-2-{[(tert-butoxy)carbonyl]amino}-4-[(4-methylbenzenesulfonyl)oxy]butanoate
• IUPAC Traditional name: ethyl (2S)-2-[(tert-butoxycarbonyl)amino]-4-[(4-methylbenzenesulfonyl)oxy]butanoate
• Synonyms: N-[(1,1-Dimethylethoxy)carbonyl]-L-homoserine Methyl Ester 4-Methylbenzenesulfonate; (S)-N-Boc-L-homoserine Methyl Ester Tosylate; N-[(1,1-Dimethylethoxy)carbonyl]-L-homoserine Ethyl Ester 4-Methylbenzenesulfonate; (S)-N-Boc-L-homoserine Ethyl Ester Tosylate

Database IDs

• CAS Number: 120042-09-3; 1331892-89-7
• PubChem SID: 162256725
• PubChem CID: 57374471

CALCULATED PROPERTIES

• Acid pKa: 12.735205
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 2.9932497
• LogD (pH = 7.4): 2.9932477
• Log P: 2.9932497
• Molar Refractivity: 99.2398 cm^3
• Polarizability: 39.945087 Å^3
• Polar Surface Area: 108.0 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Pale Yellow Semisolid

DETAILS

Toronto Research Chemicals - B656260

Used in the synthesis of the functionalizable methionine surrogate azidohomoalanine using Boc-homoserine as precursor.

REFERENCES

• Mangold, J., et al.: Mutat. Res., 216, 27 (1989)
• Link, A., et al.: Nat. Protoc., 2, 1879 (1989)