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CS-W001157 4
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(2S,4R)-4-Amino-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid

  • CAS No. 132622-69-6

  • Cat. No. CS-0109945
  • Purity≥95%
  • MDL No.MFCD05664215

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

(2S,4R)-4-Amino-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid|CS-0109945

Structure of 132622-69-6

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General Information

  • CAS No. 132622-69-6
  • Cat. No. CS-0109945
  • Purity ≥95%
  • MDL No. MFCD05664215
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₁₈N₂O₄
  • Molecular Weight 230.26
  • Synonym(s) (2S,4R)-1-Boc-4-amino-pyrrolidine-2-carboxylic acid
  • SMILES O=C(N1[C@H](C(O)=O)C[C@@H](N)C1)OC(C)(C)C

Description

This chiral pyrrolidine derivative features a protected amino group and carboxylic acid functionality, enabling direct incorporation into peptide synthesis. The (2S,4R) stereochemistry ensures high enantioselectivity in downstream conjugations, while the tert-butoxycarbonyl group provides stability under standard conditions.

Application

(2S,4R)-4-Amino-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid serves as a stereochemically defined building block for the synthesis of pyrrolidine-based peptidomimetics and bioactive heterocycles. The protected amine and carboxylic acid functionalities enable orthogonal derivatization, while the (2S,4R) configuration ensures high diastereoselectivity in downstream transformations. Its bench-stable tert-butyl carbamate group facilitates purification and compatibility with standard coupling protocols, making it well-suited for medicinal chemistry campaigns requiring precise stereocontrol.

Synthesis

  • Route1

    References

    • US2008/107623 A1, ; Page/Page column 75-76 ;
  • Route2
    • null|null
      185304-19-2
    • ~97%
    • In-stock
      (2S,4R)-4-Amino-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid|CS-0109945
      132622-69-6

    References

    • Fisher, Abigail; Mann, Amandeep; Verma, Vaneeta; Thomas, Nancy; Mishra, Ram K.; Johnson, Rodney L. Journal of Medicinal Chemistry, 2006 , vol. 49, # 1 p. 307 - 317
  • Route3
    • null|null
      132622-68-5
    • ~65%
    • In-stock
      (2S,4R)-4-Amino-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid|CS-0109945
      132622-69-6

    References

    • Webb, Thomas R.; Eigenbrot, Charles Journal of Organic Chemistry, 1991 , vol. 56, # 9 p. 3009 - 3016

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   92.86
  • LogP   0.4077
  • H_Acceptors   4
  • H_Donors   2
  • Rotatable_Bonds   1

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