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CAS 20866-46-0

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N,N'-Di-tert-butoxycarbonyl-L-histidine

Description:
N,N'-Di-tert-butoxycarbonyl-L-histidine is a derivative of the amino acid histidine, characterized by the presence of two tert-butoxycarbonyl (Boc) protecting groups attached to the nitrogen atoms of the amino group. This compound is typically used in peptide synthesis and other organic chemistry applications due to its ability to protect the amino functionality during reactions. The tert-butoxycarbonyl groups are stable under a variety of conditions but can be removed under acidic conditions, allowing for the selective deprotection of the amino groups when needed. The presence of the histidine moiety imparts unique properties, such as the ability to participate in coordination chemistry and enzymatic reactions, owing to the imidazole side chain. Additionally, the compound is generally soluble in organic solvents, making it suitable for various synthetic applications. Its molecular structure contributes to its stability and reactivity, making it a valuable intermediate in the synthesis of more complex molecules, particularly in the field of medicinal chemistry and peptide research.
Formula:C16H25N3O6
InChI:InChI=1/C16H25N3O6/c1-15(2,3)24-13(22)18-11(12(20)21)7-10-8-19(9-17-10)14(23)25-16(4,5)6/h8-9,11H,7H2,1-6H3,(H,18,22)(H,20,21)/t11-/m0/s1
SMILES:CC(C)(C)OC(=N[C@@H](Cc1cn(cn1)C(=O)OC(C)(C)C)C(=O)O)O
Synonyms:
  • Boc-His(Boc)-OH
  • (S)-3-(1-(tert-Butoxycarbonyl)-1H-imidazol-4-yl)-2-(tert-butoxycarbonylamino)propanoic acid
  • N,1-bis(tert-butoxycarbonyl)-L-histidine
  • N,1-Bis-Boc-L-histidine
  • Boc-His(Boc)-OH・Benzene
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