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(r)-3-(((Benzyloxy)carbonyl)amino)-5-(tert-butoxy)-5-oxopentanoic acid

  • CAS No. 83436-45-7

  • Cat. No. CS-0672670
  • Molecule weight337.37
  • Purity≥96%
  • MDL No.MFCD06201022

*For research and further manufacturing use only, not for direct human use.

(r)-3-(((Benzyloxy)carbonyl)amino)-5-(tert-butoxy)-5-oxopentanoic acid|CS-0672670

Structure of 83436-45-7

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General Information

  • CAS No. 83436-45-7
  • Cat. No. CS-0672670
  • Purity ≥96%
  • MDL No. MFCD06201022
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₇H₂₃NO₆
  • Molecular Weight 337.37
  • Synonym(s) None
  • SMILES CC(C)(C)OC(=O)C[C@@H](CC(=O)O)NC(=O)OCC1=CC=CC=C1

Description

(r)-3-(((Benzyloxy)carbonyl)amino)-5-(tert-butoxy)-5-oxopentanoic acid features a chiral center at the 3-position, enabling stereoselective synthesis in peptide and macrocyclic compound construction. The benzyloxycarbonyl (Cbz) group provides orthogonal protection for primary amines, while the tert-butoxy carbonyl moiety offers stable, acid-labile protection. This bifunctional scaffold integrates seamlessly into complex molecular architectures under standard bench conditions.

Application

(r)-3-(((Benzyloxy)carbonyl)amino)-5-(tert-butoxy)-5-oxopentanoic acid serves as a versatile building block for the synthesis of bioactive heterocycles and peptide derivatives. Its orthogonal functionality—comprising a carbobenzoxy (Cbz) protected amine, a ketone, and a tert-butyl ester—enables sequential transformations under standard conditions. The molecule exhibits excellent bench stability and facilitates efficient purification via standard chromatographic methods, making it well-suited for iterative synthetic workflows in medicinal chemistry and process development.

Safety Information

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GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H302-H312-H315-H319-H332-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362-P405-P501

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Computational Chemistry Data

  • TPSA   101.93
  • LogP   2.4879
  • H_Acceptors   5
  • H_Donors   2
  • Rotatable_Bonds   7

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