N-Cbz-O-tert-Butyl-L-serine, CAS No. 1676-75-1

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1676-75-1

Catalog No. EBD3513

CAS 1676-75-1

Name N-Cbz-O-tert-Butyl-L-serine

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Basic Information

Synonyms: N-Cbz-O-tert-Butyl-L-serine N-Z-O-tert-butyl-L-serine N-cbz-O-T-butyl-L-serine Z-Ser(tBu)-OH Z-Ser(But)-OH Carbobenzoxybutylserine N-Carbobenzoxy-O-tert-butyl-L-serine N-[(benzyloxy)carbonyl]-O-tert-butylserine N-[(benzyloxy)carbonyl]-O-tert-butyl-L-serine N-[(benzyloxy)carbonyl]-O-tert-butyl-D-serine Z-O-tert.butyl-L-serine n-alpha-benzyloxycarbonyl-o-tert-butyl-l-serine n-alpha-carbobenzoxy-o-t-butyll-serine n-alpha-cbz-o-t-butyl-l-serine z-l-ser(tbu)-oh z-o-t-butyl-l-serine

Molecular Formula: C15H21NO5

Molecular Weight: 295.33

MDL Number: MFCD00038275

Categories: Medicinal Chemistry > Pharmaceutical Intermediates > Drug Synthesis Building Blocks

Product Description:

N-Carbobenzoxy-O-tert-butyl-L-serine is a protected derivative of the natural amino acid L-serine. It features two orthogonal protecting groups: the N-terminal benzyloxycarbonyl (Cbz) group and the O-terminal tert-butyl (t-Bu) group. This specific protection pattern makes it a crucial chiral building block in peptide synthesis, particularly for the controlled introduction of serine residues. Its primary application is as a key intermediate in the solid-phase and solution-phase synthesis of complex peptides and peptidomimetics. The Cbz group is commonly removed under mild hydrogenolytic conditions, while the tert-butyl ether protecting group on the serine side chain is stable to hydrogenolysis but can be cleaved under acidic conditions. This differential stability allows for sequential deprotection strategies, which is essential for constructing peptides with specific post-translational modifications or for segment condensation approaches. This compound is widely used in pharmaceutical research for the development of therapeutic peptides and as a precursor in the synthesis of more complex bioactive molecules. It is a standard item in catalogs of fine chemicals and advanced pharmaceutical intermediates.

Physical Properties

Melting Point: 148 °C

Boiling Point: 465.3 °C at 760 mmHg

Flash Point: 235.2 °C

Density: 1.174 g/cm3

Refractivity: 20.5 ° (C=1, EtOH)

Storage: -15°C