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CAS 205445-55-2

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N-(tert-butoxycarbonyl)-3,4,5-trifluoro-D-phenylalanine

Description:
N-(tert-butoxycarbonyl)-3,4,5-trifluoro-D-phenylalanine, commonly referred to as Boc-D-Tyr(Trif)-OH, is an amino acid derivative characterized by the presence of a tert-butoxycarbonyl (Boc) protecting group and three fluorine atoms substituted on the aromatic ring of the phenylalanine structure. This compound is typically used in peptide synthesis and medicinal chemistry due to its unique electronic properties imparted by the trifluoromethyl groups, which can enhance the lipophilicity and metabolic stability of peptides. The Boc group serves as a protective moiety that can be removed under acidic conditions, allowing for selective deprotection during synthetic processes. The trifluoromethyl substituents can influence the compound's biological activity and interactions with receptors or enzymes. Additionally, the presence of the D-configuration indicates that this amino acid is a stereoisomer, which can be crucial in determining the biological activity of peptides in which it is incorporated. Overall, this compound is valuable in the development of pharmaceuticals and in the study of structure-activity relationships in drug design.
Formula:C14H16F3NO4
InChI:InChI=1/C14H16F3NO4/c1-14(2,3)22-13(21)18-10(12(19)20)6-7-4-8(15)11(17)9(16)5-7/h4-5,10H,6H2,1-3H3,(H,18,21)(H,19,20)/t10-/m1/s1
SMILES:CC(C)(C)OC(=N[C@H](Cc1cc(c(c(c1)F)F)F)C(=O)O)O
Synonyms:
  • Boc-D-3,4,5-Trifluorophenylalanine
  • Boc-D-Phe(3,4,5-TriF)-OH
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