Boc-O-tert-butyl-L-serine dicyclohexylamine salt, CAS No. 18942-50-2

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18942-50-2

Catalog No. EBD48352

CAS 18942-50-2

Name Boc-O-tert-butyl-L-serine dicyclohexylamine salt

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Basic Information

Synonyms: Boc-Ser(tBu)-OHdicyclohexylaminesalt N-(tert-Butoxycarbonyl)-O-tert-butyl-L-serinedicyclohexylaminesalt Boc-O-tert-butyl-L-serinedicyclohexylaminesalt Boc-O-T-Butyl-L-SerineDchaSalt Boc-O-T-Butyl-L-SerineDicyclohexylammoniumSalt Boc-O-Tert-Butyl-L-SerineDchaSalt Boc-Serine(Tbu)-OhDcha Boc-Ser(Tbu)-OhDcha N-Alpha-T-Butoxycarbonyl-O-T-Butyl-L-SerineDicyclohexylammoniumSalt N-Alpha-T-Boc-O-T-Butyl-L-Serine Boc-Ser(tBu)-OH.DCHA N-cyclohexylcyclohexanaminium(2S)-3-tert-butoxy-2-[(tert-butoxycarbonyl)amino]propanoate Boc-Ser(tBu)-OH·DCHA Boc-Ser(tBu)-OH . DCHA

Molecular Formula: C24H46N2O5

Molecular Weight: 442.63

MDL Number: MFCD00065590

Categories: Medicinal Chemistry > Pharmaceutical Intermediates > Chiral Intermediates

Product Description:

N-Boc-O-t-butyl-L-serine dicyclohexylamine salt is a protected derivative of the natural amino acid L-serine. It features two orthogonal protecting groups: the acid-labile tert-butoxycarbonyl (Boc) group on the amine and the acid-labile tert-butyl (t-Bu) group on the hydroxyl side chain. The compound is isolated as a dicyclohexylamine (DCHA) salt, which enhances its crystallinity, stability, and handling properties. This compound serves as a crucial chiral building block in peptide synthesis and medicinal chemistry. The Boc and t-Bu protecting groups are stable under basic conditions and can be selectively removed under mild acidic conditions (e.g., trifluoroacetic acid), allowing for the sequential and controlled deprotection during the synthesis of complex peptides or peptide mimetics. Its primary application is in the synthesis of serine-containing peptides and as a key intermediate for the preparation of more complex, biologically active molecules, including potential drug candidates and pharmaceutical intermediates. The DCHA salt form is preferred for purification and storage, as it often yields a crystalline solid that is easier to isolate with high purity compared to the free acid. This makes it a valuable and reliable reagent for research and development in organic synthesis and pharmaceutical manufacturing.

Physical Properties

Melting Point: 161-164 °C

Boiling Point: 571.1 °C at 760 mmHg

Flash Point: 299.2 °C

Storage: 2-8°C