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CAS 16159-70-9

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boc-D-phenylalanine 4-nitrophenyl ester

Description:
Boc-D-phenylalanine 4-nitrophenyl ester is a chemical compound that serves as a protected form of the amino acid D-phenylalanine, commonly used in peptide synthesis. The "Boc" (tert-butyloxycarbonyl) group is a protective group that shields the amino group of the phenylalanine, facilitating selective reactions without interference from the amine. The 4-nitrophenyl ester moiety enhances the compound's reactivity, making it useful in coupling reactions where the release of the phenylalanine residue is desired. This compound is typically a white to off-white solid and is soluble in organic solvents such as dichloromethane and dimethylformamide. Its stability under standard laboratory conditions allows for ease of handling and storage. The presence of the nitro group also contributes to its electronic properties, potentially influencing its reactivity in various chemical transformations. Overall, Boc-D-phenylalanine 4-nitrophenyl ester is valuable in organic synthesis, particularly in the field of medicinal chemistry and peptide development.
Formula:C20H22N2O6
InChI:InChI=1/C20H22N2O6/c1-20(2,3)28-19(24)21-17(13-14-7-5-4-6-8-14)18(23)27-16-11-9-15(10-12-16)22(25)26/h4-12,17H,13H2,1-3H3,(H,21,24)/t17-/m1/s1
SMILES:CC(C)(C)OC(=N[C@H](Cc1ccccc1)C(=O)Oc1ccc(cc1)N(=O)=O)O
Synonyms:
  • Boc-D-Phe-ONp
  • 4-nitrophenyl N-(tert-butoxycarbonyl)-D-phenylalaninate
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