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CS-W001157 4
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(2S,4S)-1-((Benzyloxy)carbonyl)-4-hydroxypyrrolidine-2-carboxylic acid

  • CAS No. 13504-86-4

  • Cat. No. CS-0054528
  • Purity≥98%
  • MDL No.None

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

(2S,4S)-1-((Benzyloxy)carbonyl)-4-hydroxypyrrolidine-2-carboxylic acid|CS-0054528

Structure of 13504-86-4

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General Information

  • CAS No. 13504-86-4
  • Cat. No. CS-0054528
  • Purity ≥98%
  • MDL No. None
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₃H₁₅NO₅
  • Molecular Weight 265.26
  • Synonym(s) None
  • SMILES O[C@H]1C[C@H](N(C1)C(=O)OCC1=CC=CC=C1)C(O)=O

Description

This chiral pyrrolidine derivative features a bench-stable, moisture-tolerant hydroxyl group flanked by a protected carboxylic acid and benzylated nitrogen. The (2S,4S) stereochemistry enables precise incorporation into peptide backbones and complex heterocycles. Its solubility profile supports efficient coupling reactions under standard conditions, making it a reliable building block for medicinal chemistry campaigns targeting bioactive scaffolds.

Application

(2S,4S)-1-((Benzyloxy)carbonyl)-4-hydroxypyrrolidine-2-carboxylic acid serves as a stereochemically defined building block for the synthesis of bioactive pyrrolidine-containing scaffolds. The hydroxyl group enables facile derivatization via esterification or ether formation, while the protected carboxylic acid allows for selective peptide coupling. Its bench-stable, crystalline nature and orthogonal functional group tolerance facilitate efficient incorporation into complex molecular architectures, including peptidomimetics and heterocyclic APIs.

Synthesis

  • Route1
    • null|null
      501-53-1
    • In-stock
      (2S,4S)-4-Hydroxypyrrolidine-2-carboxylic acid|CS-W009077
      618-27-9
    • ~81%
    • In-stock
      (2S,4S)-1-((Benzyloxy)carbonyl)-4-hydroxypyrrolidine-2-carboxylic acid|CS-0054528
      13504-86-4

    References

    • Brown, Allan G.; Moss, Stephen F.; Southgate, Robert Tetrahedron Letters, 1994 , vol. 35, # 3 p. 451 - 454
  • Route2
    • null|null
      170159-62-3
    • ~91%
    • In-stock
      (2S,4S)-1-((Benzyloxy)carbonyl)-4-hydroxypyrrolidine-2-carboxylic acid|CS-0054528
      13504-86-4

    References

    • Seki, Masahiko; Matsumoto, Kazuo Bioscience, Biotechnology, and Biochemistry, 1995 , vol. 59, # 6 p. 1161 - 1162
  • Route3

    References

    • Bulletin of the Chemical Society of Japan, , vol. 72, # 12 p. 2737 - 2754

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   87.07
  • LogP   0.843
  • H_Acceptors   4
  • H_Donors   2
  • Rotatable_Bonds   3

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