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(R)-1-(tert-Butoxycarbonyl)-4,4-difluoropyrrolidine-2-carboxylic acid

  • CAS No. 536747-87-2

  • Cat. No. CS-0053507
  • Molecule weight251.23
  • Purity≥95%
  • MDL No.MFCD08272893

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

(R)-1-(tert-Butoxycarbonyl)-4,4-difluoropyrrolidine-2-carboxylic acid|CS-0053507

Structure of 536747-87-2

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General Information

  • CAS No. 536747-87-2
  • Cat. No. CS-0053507
  • Purity ≥95%
  • MDL No. MFCD08272893
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₁₅F₂NO₄
  • Molecular Weight 251.23
  • Synonym(s) 4,4-Difluoro-1-Boc-D-proline
  • SMILES CC(C)(C)OC(=O)N1CC(F)(F)C[C@@H]1C(O)=O

Description

This chiral pyrrolidine derivative features a bench-stable tert-butyl carbamate protecting group and two fluorine atoms at the C4 position, enhancing metabolic stability and modulating electronic properties. The difluoropyrrolidine scaffold integrates readily into peptide-based scaffolds, enabling access to constrained bioactive motifs with improved membrane permeability and target affinity.

Application

(R)-1-(tert-Butoxycarbonyl)-4,4-difluoropyrrolidine-2-carboxylic acid serves as a conformationally constrained, fluorinated proline analog enabling precise stereocontrol in peptide synthesis. The difluoropyrrolidine core enhances metabolic stability and modulates backbone rigidity, while the Boc group permits straightforward deprotection and coupling. This building block exhibits excellent bench stability, tolerance to diverse reaction conditions, and facilitates the construction of bioactive peptidomimetics and macrocyclic scaffolds in medicinal chemistry workflows.

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-H315-H319-H335
Precautionary Statements : P261-P280-P302+P352

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Computational Chemistry Data

  • TPSA   66.84
  • LogP   1.7157
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   1

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