Description

Dicyclohexylamine (S)-4-(((benzyloxy)carbonyl)amino)-2-((tert-butoxycarbonyl)amino)butanoate (CAS: 16947-89-0) is a high-purity, specialized chemical compound designed for advanced research and pharmaceutical applications. With the molecular formula C₂₉H₄₇N₃O₆, this product is a dicyclohexylamine salt derivative of a protected diaminobutyric acid, featuring both tert-butoxycarbonyl (Boc) and benzyloxycarbonyl (Z) protecting groups. It is ideal for peptide synthesis, particularly in the construction of complex peptide chains requiring orthogonal protection strategies. The compound is supplied as a white to off-white crystalline powder, rigorously tested for purity (>98% by HPLC) and stability, ensuring reproducibility in sensitive experiments. Store under inert conditions at 2-8°C to maintain integrity.

Properties

• CAS Number: 16947-89-0
• Complexity: 571
• IUPAC Name: (2S)-4-(benzyloxycarbonylamino)-2-(tert-butoxycarbonylamino)butanoic acid;N-cyclohexylcyclohexanamine
• InChI: InChI=1S/C17H24N2O6.C12H23N/c1-17(2,3)25-16(23)19-13(14(20)21)9-10-18-15(22)24-11-12-7-5-4-6-8-12;1-3-7-11(8-4-1)13-12-9-5-2-6-10-12/h4-8,13H,9-11H2,1-3H3,(H,18,22)(H,19,23)(H,20,21);11-13H,1-10H2/t13-;/m0./s1
• InChI Key: CBSVEVKFQHTZSP-ZOWNYOTGSA-N
• Exact Mass: 533.34648623
• Molecular Formula: C29H47N3O6
• Molecular Weight: 533.7
• SMILES: CC(C)(C)OC(=O)N[C@@H](CCNC(=O)OCC1=CC=CC=C1)C(=O)O.C1CCC(CC1)NC2CCCCC2
• Topological: 126
• Monoisotopic Mass: 533.34648623
• Synonyms: 16947-89-0, Boc-Dab(Z)-OH.DCHA, Dicyclohexylamine (S)-4-(((benzyloxy)carbonyl)amino)-2-((tert-butoxycarbonyl)amino)butanoate, BOC-DAB(Z)-OH DCHA, N-cyclohexylcyclohexanamine;(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4-(phenylmethoxycarbonylamino)butanoic acid, Boc-L-Dab(Z)-OH DCHA, CBSVEVKFQHTZSP-ZOWNYOTGSA-N, MFCD00236879, Boc-L-Dab(Z)-OH*DCHA, SCHEMBL4846559, DTXSID00669959, AKOS015901315, Dicyclohexylamine(S)-4-(((benzyloxy)carbonyl)amino)-2-((tert-butoxycarbonyl)amino)butanoate, DS-14436, CS-0133022, D83049, S-16947-89-0, (2S)-4-{[(benzyloxy)carbonyl]amino}-2-[(tert-butoxycarbonyl)amino]butanoic acid N-cyclohexylcyclohexanamine, (2S)-4-{[(Benzyloxy)carbonyl]amino}-2-[(tert-butoxycarbonyl)amino]butanoic acid–N-cyclohexylcyclohexanamine (1/1), N-alpha-t-Butyloxycarbonyl-N-gamma-benZyloxycarbonyl-L-2,4-diaminobutyric acid dicyclohexylamine (Boc-L-Dab(CbZ)-OH.DCHA)

This compound serves as a critical intermediate in solid-phase peptide synthesis (SPPS), enabling the controlled incorporation of L-2,4-diaminobutyric acid residues with orthogonal protection. Its dual-protected structure allows selective deprotection for sequential peptide elongation, making it valuable for synthesizing bioactive peptides, antimicrobial agents, and constrained peptidomimetics. Researchers also utilize it in medicinal chemistry for developing protease inhibitors and targeted drug conjugates.

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