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(2S,4S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)-4-((tert-butoxycarbonyl)amino)pyrrolidine-2-carboxylic acid

  • CAS No. 221352-74-5

  • Cat. No. CS-0089867
  • Purity≥95%
  • MDL No.None

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

(2S,4S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)-4-((tert-butoxycarbonyl)amino)pyrrolidine-2-carboxylic acid|CS-0089867

Structure of 221352-74-5

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General Information

  • CAS No. 221352-74-5
  • Cat. No. CS-0089867
  • Purity ≥95%
  • MDL No. None
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₂₅H₂₈N₂O₆
  • Molecular Weight 452.50
  • Synonym(s) (2S, 4S)-BOC-4-AMINO-1-FMOC-PYRROLIDINE-2-CARBOXYLIC ACID
  • SMILES O=C(N1[C@H](C(O)=O)C[C@H](NC(OC(C)(C)C)=O)C1)OCC2C3=C(C4=C2C=CC=C4)C=CC=C3

Description

This fluorenylmethoxycarbonyl-protected pyrrolidine derivative features a sterically hindered, bench-stable scaffold ideal for peptide synthesis. The (2S,4S)-configuration ensures stereochemical fidelity, while the C-terminal carboxylic acid and Boc-protected amine enable sequential coupling in solid-phase workflows.

Application

(2S,4S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)-4-((tert-butoxycarbonyl)amino)pyrrolidine-2-carboxylic acid serves as a versatile chiral building block for peptide and heterocyclic synthesis. Its protected amine and carboxylic acid functionalities enable orthogonal deprotection and coupling strategies. The Fmoc group ensures stability under basic conditions, while the Boc-labile amine facilitates selective activation. This scaffold is well-suited for solid-phase peptide synthesis and the construction of bioactive pyrrolidine-containing compounds.

Synthesis

  • Route1
    • In-stock
      (2S,4S)-Methyl 4-((tert-butoxycarbonyl)amino)pyrrolidine-2-carboxylate|CS-0049318
      168263-82-9
    • null|null
      28920-43-6
    • ~42%
    • In-stock
      (2S,4S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)-4-((tert-butoxycarbonyl)amino)pyrrolidine-2-carboxylic acid|CS-0089867
      221352-74-5

    References

    • Umashankara; Babu, I Ramesh; Ganesh, Krishna N Chemical communications (Cambridge, England), 2003 , # 20 p. 2606 - 2607
  • Route2
    • null|null
      853063-23-7
    • ~%
    • In-stock
      (2S,4S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)-4-((tert-butoxycarbonyl)amino)pyrrolidine-2-carboxylic acid|CS-0089867
      221352-74-5

    References

    • Journal of Medicinal Chemistry, , vol. 48, # 9 p. 3280 - 3289
  • Route3

    References

    • Journal of Medicinal Chemistry, , vol. 48, # 9 p. 3280 - 3289

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-H317
Precautionary Statements : P261-P264-P270-P272-P280-P302+P352-P330-P362+P364-P501

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Computational Chemistry Data

  • TPSA   105.17
  • LogP   3.9877
  • H_Acceptors   5
  • H_Donors   2
  • Rotatable_Bonds   4

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