Description

Dicyclohexylamine (S)-2-((tert-butoxycarbonyl)amino)pent-4-enoate (CAS: 143979-15-1) is a high-purity chemical compound with the molecular formula C₂₂H₄₀N₂O₄. This specialized reagent is widely used in peptide synthesis and organic chemistry research as a protected amino acid derivative. The product is supplied as a dicyclohexylammonium salt of Boc-L-Allylglycine, ensuring enhanced stability and solubility for synthetic applications. With a purity of ≥98% (TLC), this white to off-white crystalline powder is ideal for critical pharmaceutical and bioconjugation research. The compound features both tert-butoxycarbonyl (Boc) protection for the amino group and an allyl side chain, making it particularly valuable for orthogonal protection strategies in solid-phase peptide synthesis (SPPS). Proper storage at 2-8°C in a tightly sealed container is recommended to maintain optimal stability.

Properties

• CAS Number: 143979-15-1
• Complexity: 371
• IUPAC Name: (2S)-2-(tert-butoxycarbonylamino)pent-4-enoic acid;N-cyclohexylcyclohexanamine
• InChI: InChI=1S/C12H23N.C10H17NO4/c1-3-7-11(8-4-1)13-12-9-5-2-6-10-12;1-5-6-7(8(12)13)11-9(14)15-10(2,3)4/h11-13H,1-10H2;5,7H,1,6H2,2-4H3,(H,11,14)(H,12,13)/t;7-/m.0/s1
• InChI Key: VMCGMPITVQIMGK-ZLTKDMPESA-N
• Exact Mass: 396.29880776
• Molecular Formula: C22H40N2O4
• Molecular Weight: 396.6
• SMILES: CC(C)(C)OC(=O)N[C@@H](CC=C)C(=O)O.C1CCC(CC1)NC2CCCCC2
• Topological: 87.7
• Monoisotopic Mass: 396.29880776
• Synonyms: 143979-15-1, Dicyclohexylamine (S)-2-((tert-butoxycarbonyl)amino)pent-4-enoate, Boc-allyl-Gly-OH (dicyclohexylammonium) salt, Boc-Allyl-L-glycine dicyclohexylammonium salt, Boc-L-Allylglycine.DCHA, MFCD01321013, Boc-L-2-allylglycine dicyclohexylamine salt, N-cyclohexylcyclohexanamine;(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]pent-4-enoic acid, Boc-L-Allylglycine-DCHA, C22H40N2O4, Boc-L-Allylglycine dicyclohexylaminoium salt, Boc-L-allylglycine . DCHA, Boc-Algly-OH.DCHA, SCHEMBL25363057, DTXSID10373176, AKOS015948714, AC-7944, CS-W009390, HY-W008674, AS-11357, DA-71639, Boc-allyl-Gly-OH dicyclohexylammonium salt, D82221, Boc-L-Allylglycine DCHA (Boc-L-Gly(All)-OH.DCHA), Boc-allyl-Gly-OH (dicyclohexylammonium) salt, >=98.0% (TLC), Dicyclohexylamine(S)-2-((tert-butoxycarbonyl)amino)pent-4-enoate, (2S)-2-[(tert-Butoxycarbonyl)amino]pent-4-enoic acid–N-cyclohexylcyclohexanamine (1/1), (S)-2-((tert-Butoxycarbonyl)amino)pent-4-enoic acid dicyclohexylammonium salt

This compound serves as a key intermediate in the synthesis of modified peptides and peptidomimetics, particularly where allyl-protected glycine derivatives are required. It finds application in medicinal chemistry for the development of novel therapeutics and in materials science for bioconjugation strategies. Researchers utilize this reagent in SPPS when orthogonal protection of the amino acid backbone is needed. The allyl group enables further functionalization via click chemistry or palladium-catalyzed reactions.

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