(2S,3R)-2-{[(benzyloxy)carbonyl]amino}-3-hydroxybutanoic acid(CAS: 19728-63-3)

(2S,3R)-2-{[(Benzyloxy)carbonyl]amino}-3-hydroxybutanoic acid is a white crystalline solid with a molecular weight of approximately 308.34 g/mol. It has low water solubility and exhibits basic properties due to the amine functionality. The compound is less reactive compared to other carboxylic acids due to the protecting group. It is stable under normal laboratory conditions but should be protected from strong acids and bases.

(2S,3R)-2-{[(Benzyloxy)carbonyl]amino}-3-hydroxybutanoic acid can be synthesized via a multi-step process involving the protection of the amino group, followed by amidation and subsequent deprotection. Common starting materials include benzyloxycarbonyl chloride and 3-amino-2-hydroxybutanoic acid. The reaction typically involves the use of triethylamine as a base and is conducted under mild conditions to achieve high yield and selectivity.

(2S,3R)-2-{[(Benzyloxy)carbonyl]amino}-3-hydroxybutanoic acid finds applications in the pharmaceutical industry, particularly in the synthesis of prodrugs and intermediates for drug development. It is also used in the chemical and polymer industries for the production of functionalized polymers and as a precursor in the synthesis of various compounds with specific reactivity profiles.

When handling (2S,3R)-2-{[(Benzyloxy)carbonyl]amino}-3-hydroxybutanoic acid, it is important to wear appropriate personal protective equipment (PPE) such as gloves, goggles, and a lab coat. Work in a well-ventilated area or a fume hood due to the potential for off-gassing of the amine group. Spills should be cleaned up with appropriate absorbents and disposed of according to local regulations. Always consult the Material Safety Data Sheet (MSDS) for detailed handling and safety information.