In the realm of organic chemistry, understanding the fundamental properties and synthesis methods of key intermediates is crucial for developing efficient and innovative chemical processes. O-tert-Butyl-L-serine, known by its abbreviation H-Ser(tBu)-OH and identified by CAS number 18822-58-7, is one such compound that warrants detailed examination. As a protected amino acid derivative, its chemical characteristics and synthesis pathways are fundamental to its wide applicability in fields ranging from pharmaceuticals to materials science.

The molecular structure of H-Ser(tBu)-OH is derived from L-serine, featuring an alpha-amino group, a carboxyl group, and a side chain containing a hydroxyl group protected as a tert-butyl ether. Its chemical formula is C7H15NO3, with a molar mass of approximately 161.2 g/mol. Typically appearing as a white powder, it exhibits good solubility in water and common organic solvents, which facilitates its use in various reaction environments. The presence of the tert-butyl group not only shields the hydroxyl functionality but also influences the compound's solubility and reactivity profile, making it distinct from unprotected serine.

The synthesis of H-Ser(tBu)-OH generally involves the protection of the hydroxyl group of L-serine. One common method is the reaction of L-serine with isobutylene or tert-butyl alcohol under acidic conditions, often utilizing catalysts to promote the etherification. Alternatively, L-serine can be first N-protected (e.g., with Fmoc or Boc groups), followed by the tert-butylation of the hydroxyl group, and then subsequent removal of the N-protecting group if the free amine form is desired. Manufacturers invest in optimizing these synthetic routes to ensure high yields, purity, and cost-effectiveness when producing this intermediate for sale.

The chemical properties of H-Ser(tBu)-OH make it an invaluable component in further chemical transformations. The tert-butyl ether is relatively stable to basic conditions, mild acidic conditions, and many nucleophilic reagents, which is essential during multi-step synthesis. However, it can be readily cleaved using strong acids like trifluoroacetic acid (TFA) or HCl in organic solvents, regenerating the free hydroxyl group of serine. This selective deprotection capability is key to its utility in building complex molecular structures, especially in the synthesis of peptides and pharmaceuticals where precise control over functional group exposure is critical.

When considering the purchase of H-Ser(tBu)-OH, understanding these chemical properties and synthesis methods provides valuable insight for procurement managers and chemists. Knowing how the compound is made and its stability characteristics helps in evaluating supplier quality and ensuring the intermediate performs as expected in downstream applications. Exploring different suppliers who can offer this compound ensures access to reliable and well-characterized materials for chemical manufacturing and research.

In essence, O-tert-Butyl-L-serine (H-Ser(tBu)-OH) is a product of specific chemical design, engineered for enhanced utility in synthesis. Its chemical properties, particularly the protected hydroxyl group, and established synthesis routes underscore its importance as a versatile intermediate. Understanding these aspects empowers chemists and procurement professionals to effectively utilize and source this critical compound.