(S)-N-Carbobenzyloxy-4-amino-2-hydroxybutyric acid, CAS No. 40371-50-4

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40371-50-4

Catalog No. EBD11207

CAS 40371-50-4

Name (S)-N-Carbobenzyloxy-4-amino-2-hydroxybutyric acid

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Basic Information

Synonyms: CBZ-S-(+)-L-HABA (2S)-4-{[(benzyloxy)carbonyl]amino}-2-hydroxybutanoicacid 4-{[(benzyloxy)carbonyl]amino}-2-hydroxybutanoicacid (2S)-4-{[(benzyloxy)carbonyl]amino}-2-hydroxybutanoate (2R)-4-{[(benzyloxy)carbonyl]amino}-2-hydroxybutanoicacid (S)-4-BENZYLOXYCARBONYLAMINO-2-HYDROXYBUTYR ACIDOL-4BENZYLOXYCARBONYL-AMINO-2HYDROXYBUTYRIC L--a-Hydroxy-BenzyloxycarbonylaminoButyricAcid(CBZ-HABA) (S)-(+)-Z-4-AMINO-2-HYDROXYBUTYRICACID (S)-CBZ-HABA (S)-N-CARBOBENZYLOXY-4-AMINO-2-HYDROXYBUTYRICACID (S)-(-)-GAMMA-N-CBZ-AMINO-ALPHA-HYDROXYBUTYRICACID (S)-4-BENZYLOXYCARBONYLAMINO-2-HYDROXYBUTYRICACID (s)-2-hydroxy-4-[[(phenylmethoxy)carbonyl]amino]butyricacid L-(-)-ALPHA-HYDROXY-GAMMA-BENZYLOXYCARBONYLAMINOBUTYRICACID CBZ-HABA

Molecular Formula: C12H15NO5

Molecular Weight: 253.25

MDL Number: MFCD00209957

Categories: Medicinal Chemistry > Pharmaceutical Intermediates > Drug Synthesis Building Blocks Medicinal Chemistry > Biochemicals and Life Science Reagents > Amino Acids and Derivatives

Product Description:

4-(((Benzyloxy)carbonyl)amino)-2-hydroxybutanoic acid is a protected amino acid derivative. Its structure features a 2-hydroxybutanoic acid backbone with a benzyloxycarbonyl (Cbz) protecting group on the amine functionality. This compound serves as a crucial chiral building block in organic synthesis, particularly for the preparation of complex molecules. The primary application of this compound is in the synthesis of biologically active peptides and peptidomimetics. It is notably used as a key intermediate in the production of the angiotensin-converting enzyme (ACE) inhibitor, Cilazapril, a medication for treating hypertension and heart failure. The Cbz group provides orthogonal protection for the amine during peptide coupling steps, and the hydroxyl group offers a handle for further functionalization. As a specialized chiral synthon, it is a valuable reagent in medicinal chemistry research for constructing molecules with specific stereochemistry. Its use is confined primarily to pharmaceutical research and development as a high-value intermediate, rather than as a bulk commodity or general-purpose reagent.

Physical Properties

Melting Point: 75-78 °C(lit.)

Boiling Point: 521.2 ºC at 760 mmHg

Flash Point: 269 ºC

Density: 1.311 g/cm3

Analytical Data

Appearance: off-white crystalline powder