(4S,5R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-4-phenyloxazolidine-5-carboxylic acid CAS: 143527-70-2
Catalog Number | XD94109 |
Product Name | (4S,5R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-4-phenyloxazolidine-5-carboxylic acid |
CAS | 143527-70-2 |
Molecular Formula | C17H23NO5 |
Molecular Weight | 321.37 |
Storage Details | Ambient |
Product Specification
Appearance | White powder |
Assay | 99% min |
The compound (4S,5R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-4-phenyloxazolidine-5-carboxylic acid, commonly referred to as Boc-phenylglycine, has significant importance in the field of organic synthesis and peptide chemistry.Boc-phenylglycine belongs to a class of compounds known as amino acid derivatives. It is characterized by the presence of an oxazolidine ring, which imparts unique properties and reactivity to the compound. The tert-butoxycarbonyl (Boc) group, a protecting group often used in peptide synthesis, is attached to the amino group of phenylglycine.One of the primary uses of Boc-phenylglycine is in the synthesis of peptides. Peptides are short chains of amino acids that play crucial roles in biological processes and have immense therapeutic potential. Boc-phenylglycine, as an amino acid derivative, can be incorporated into peptide sequences during solid-phase peptide synthesis.Solid-phase peptide synthesis (SPPS) is a widely employed method for the preparation of peptides. The Boc-protecting group on the amino group of Boc-phenylglycine allows the selective addition of other amino acids to form a peptide chain on a solid support. The Boc group can be easily removed under mild acidic conditions, enabling the addition of subsequent amino acids to elongate the peptide chain. This iterative process allows for the synthesis of peptides with precise sequences that are essential for their biological activity.Boc-phenylglycine is also utilized as a chiral building block in organic synthesis and medicinal chemistry. Its stereochemistry can be harnessed to create enantiomerically pure compounds, which are important in drug discovery and development. By utilizing the chirality of Boc-phenylglycine, chemists can synthesize molecules with specific three-dimensional arrangements, which can significantly impact their biological activity and pharmacological properties.Furthermore, Boc-phenylglycine and its derivatives find applications beyond peptide synthesis. They can serve as starting materials for the synthesis of natural products, pharmaceutical intermediates, and peptidomimetics - compounds that mimic the structure and function of peptides.In summary, (4S,5R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-4-phenyloxazolidine-5-carboxylic acid (Boc-phenylglycine) is a versatile compound widely used in the fields of organic synthesis and peptide chemistry. Its inclusion in peptide sequences during solid-phase peptide synthesis allows for the preparation of various peptides with precise sequences. Its ability to act as a chiral building block enables the synthesis of enantiomerically pure compounds. Moreover, Boc-phenylglycine and its derivatives are employed in the synthesis of natural products, pharmaceutical intermediates, and peptidomimetics. Overall, Boc-phenylglycine plays a crucial role in the development of new drugs, understanding biological processes, and advancing the field of organic chemistry.