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(2S,4S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)-4-fluoropyrrolidine-2-carboxylic acid

  • CAS No. 203866-19-7

  • Cat. No. CS-0046771
  • Purity≥97%
  • MDL No.MFCD07781261

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

(2S,4S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)-4-fluoropyrrolidine-2-carboxylic acid|CS-0046771

Structure of 203866-19-7

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General Information

  • CAS No. 203866-19-7
  • Cat. No. CS-0046771
  • Purity ≥97%
  • MDL No. MFCD07781261
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₂₀H₁₈FNO₄
  • Molecular Weight 355.36
  • Synonym(s) N-Fmoc-cis-4-fluoro-L-proline
  • SMILES O=C(N1[C@H](C(O)=O)C[C@H](F)C1)OCC2C3=C(C4=C2C=CC=C4)C=CC=C3

Description

This fluorenylmethoxy carbamate-protected pyrrolidine derivative features a stereodefined (2S,4S) configuration and a fluorinated C4 position, enhancing metabolic stability. The Fmoc group enables efficient solid-phase synthesis, while the carboxylic acid moiety serves as a direct coupling handle in peptide elongation workflows.

Application

(2S,4S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)-4-fluoropyrrolidine-2-carboxylic acid serves as a stereochemically defined building block for the synthesis of fluorinated proline analogs. The Fmoc group provides orthogonal protection and facilitates purification via standard chromatographic methods. The 4-fluoro substituent enhances conformational rigidity and modulates electronic properties, enabling its use in peptide coupling reactions and the construction of bioactive heterocyclic scaffolds relevant to medicinal chemistry workflows.

Synthesis

  • Route1
    • null|null
      28920-43-6
    • In-stock
      (2S,4S)-4-Fluoropyrrolidine-2-carboxylic acid|CS-0058726
      2438-57-5
    • ~%
    • In-stock
      (2S,4S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)-4-fluoropyrrolidine-2-carboxylic acid|CS-0046771
      203866-19-7

    References

    • Angewandte Chemie - International Edition, , vol. 48, # 10 p. 1784 - 1787
  • Route2
    • null|null
      497073-96-8
    • ~87%
    • In-stock
      (2S,4S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)-4-fluoropyrrolidine-2-carboxylic acid|CS-0046771
      203866-19-7

    References

    • Tetrahedron, , vol. 58, # 42 p. 8453 - 8459
  • Route3
    • null|null
      149671-25-0
    • ~%
    • In-stock
      (2S,4S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)-4-fluoropyrrolidine-2-carboxylic acid|CS-0046771
      203866-19-7

    References

    • Tetrahedron, , vol. 58, # 42 p. 8453 - 8459

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   66.84
  • LogP   3.4325
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   3

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