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CAS 6404-31-5

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N-(Benzyloxycarbonyl)-D-proline

Description:
N-(Benzyloxycarbonyl)-D-proline, also known as Z-D-proline, is a derivative of the amino acid proline, characterized by the presence of a benzyloxycarbonyl (Z) protecting group. This compound is typically used in peptide synthesis as a protecting group for the amino functionality, enhancing the stability and reactivity of the proline residue during chemical reactions. It is a white to off-white crystalline solid, soluble in organic solvents such as methanol and dimethyl sulfoxide, but generally insoluble in water. The presence of the benzyloxycarbonyl group imparts increased lipophilicity, making it useful in various organic synthesis applications. N-(Benzyloxycarbonyl)-D-proline is also notable for its role in the synthesis of cyclic peptides and other complex organic molecules, where the proline structure contributes to the conformational rigidity and biological activity of the resulting compounds. As with many chemical substances, proper handling and storage are essential to maintain its stability and prevent degradation.
Formula:C13H15NO4
InChI:InChI=1/C13H15NO4/c15-12(16)11-7-4-8-14(11)13(17)18-9-10-5-2-1-3-6-10/h1-3,5-6,11H,4,7-9H2,(H,15,16)/p-1/t11-/m1/s1
InChI key:InChIKey=JXGVXCZADZNAMJ-LLVKDONJSA-N
SMILES:C(OCC1=CC=CC=C1)(=O)N2[C@@H](C(O)=O)CCC2
Synonyms:
  • (+)-Z-D-proline
  • (2R)-1-(Benzyloxycarbonyl)pyrrolidine-2-carboxylic acid
  • (2R)-1-Phenylmethoxycarbonylpyrrolidine-2-carboxylic acid
  • (2R)-1-[(Benzyloxy)carbonyl]pyrrolidine-2-carboxylic acid
  • (2R)-1-[(benzyloxy)carbonyl]pyrrolidine-2-carboxylate
  • (Benzyloxycarbonyl)-<span class="text-smallcaps">D</span>-proline
  • (R)-1-(Benzyloxycarbonyl)pyrrolidine-2-carboxylic acid
  • (R)-N-BenzyloxycarbonyLproline
  • 1,2-Pyrrolidinedicarboxylic acid, 1-(phenylmethyl) ester, (2R)-
  • 1,2-Pyrrolidinedicarboxylic acid, 1-(phenylmethyl) ester, (R)-
  • See more synonyms
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