(R)-2-Benzyl-3-(tert-Butoxycarbonylamino)propanoic acid(CAS#262301-38-2)
| Hazard Symbols | Xi - Irritant |
| Risk Codes | R36 - Irritating to the eyes R43 - May cause sensitization by skin contact |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36/37 - Wear suitable protective clothing and gloves. |
Introduction
(2S)-2-Benzyl-3-[(tert-butoxycarbonyl)-amino]propanoic acid is an organic compound.It is a white solid that is stable at room temperature. It has some specific chemical properties, such as it is a racemate, i.e. it can have two stereoisomers (S and R forms) in it. It is a chiral amino acid derivative with a phenylethyl group and an alkyd functional group located on α-carbon.(2S)-2-Benzyl-3-[(tert-butoxycarbonyl)-amino]propanoic acid is commonly used as an intermediate in organic synthesis. It can also be used in the preparation of biologically active substances such as protease inhibitors.Preparation of (2S)-2-Benzyl-3-[(tert-butoxycarbonyl)-amino]propanoic acid can be performed in several steps. A common method is to start with phenylacetic acid and synthesize it through reduction, acylation, reductive amine, and aminoprotection reactions. Specific synthesis methods can be optimized as needed.Safety Information: (2S)-2-Benzyl-3-[(tert-butoxycarbonyl)-amino]propanoic acid is a chemical and proper laboratory practice should be followed. During use, wear chemical protective gloves and goggles to ensure good ventilation conditions. Avoid contact with skin and eyes, and avoid inhalation or ingestion. In case of accidental contact or ingestion, seek medical attention immediately and bring the chemical label to the hospital.
Application
(R)-2-Benzyl-3-(tert-Butoxycarbonylamino)propanoic acid (CAS 262301-38-2), also known as Boc-(R)-β²-homophenylalanine, is a chiral β²-amino acid derivative featuring a Boc-protected amine and a benzyl side chain. The unique β²-substitution pattern (with the side chain on the α-carbon) provides distinct conformational constraints and enhanced proteolytic stability compared to standard α-amino acids. This rigid, non-natural building block is primarily used as a pharmaceutical intermediate in solid‑phase peptide synthesis (SPPS) to engineer peptidomimetics and modified peptides with improved metabolic stability and target selectivity. It is particularly valuable in drug discovery for synthesizing dipeptidyl peptidase IV (DPP-4) inhibitors for type 2 diabetes, as well as renin inhibitors for hypertension and various protease-targeted therapeutics. The β-homophenylalanine scaffold is also employed in protein engineering, medicinal chemistry for optimizing lead compounds, and the development of peptide-based drugs with enhanced half-life and bioavailability. Xinchem offers custom synthesis and contract manufacturing of this high-purity (≥98%) chiral building block, available from R&D research grams to GMP commercial metric tons, with full analytical support including HPLC and MS characterization. Contact us for a competitive quote and reliable global supply.
