The field of organic synthesis, particularly in areas like medicinal chemistry and materials science, relies on a vast array of specialized building blocks. Among these, amino acid derivatives hold a prominent position. This article focuses on N-Boc-O-benzyl-L-threonine (CAS 15260-10-3), a compound that plays a crucial role in sophisticated synthetic pathways. Understanding its properties and applications is essential for researchers and procurement specialists.

N-Boc-O-benzyl-L-threonine is derived from L-threonine, one of the proteinogenic amino acids. Its structure is characterized by two key protecting groups. The 'Boc' (tert-butoxycarbonyl) group is attached to the alpha-amino nitrogen. This group is widely used in peptide synthesis due to its stability under many reaction conditions and its facile removal under acidic conditions. The second protecting group is a benzyl (Bzl) ether on the hydroxyl moiety of the threonine side chain. The benzyl group offers protection during synthesis and can be removed through hydrogenolysis or strong acid treatment.

The chemical formula of N-Boc-O-benzyl-L-threonine is C16H23NO5, with a molecular weight of approximately 309.36 g/mol. Its typical appearance is a white crystalline powder, a standard form for many high-purity organic reagents. The presence of two chiral centers in threonine means that stereochemistry is crucial. This compound is specifically the L-threonine derivative, ensuring the correct chirality for biological and pharmaceutical applications. Manufacturers often specify optical purity to guarantee the integrity of the synthesized products.

The primary application of N-Boc-O-benzyl-L-threonine is in peptide synthesis, particularly using the Boc solid-phase peptide synthesis (Boc SPPS) strategy. In this method, amino acids are sequentially attached to a solid resin support. The protecting groups on each amino acid ensure that coupling occurs only at the intended site, building the peptide chain step by step. The benzyl protection on the threonine side chain is particularly advantageous as it can withstand many coupling and deprotection cycles and is removed efficiently at the end of the synthesis.

For those looking to buy N-Boc-O-benzyl-L-threonine, it is important to source from reputable manufacturers and suppliers. Companies seeking this intermediate often require high purity (≥99.00%) to ensure successful synthetic outcomes. The availability of technical data, such as melting point, solubility, and spectral information (e.g., IR, NMR), from suppliers like those in China, is essential for quality control and process development.

In conclusion, N-Boc-O-benzyl-L-threonine is a prime example of a well-designed amino acid derivative that facilitates complex organic synthesis. Its specific protecting groups and chiral integrity make it an indispensable reagent for researchers and manufacturers in the pharmaceutical and biotechnology sectors. Understanding its chemical nature and applications ensures its effective utilization in advancing scientific discovery and product development.