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CS-W001157 4
Total: USD 88.00

N-Boc-4,4-difluoro-L-proline methyl ester

  • CAS No. 203866-17-5

  • Cat. No. CS-W001497
  • Purity≥98%
  • MDL No.MFCD03094918

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

N-Boc-4,4-difluoro-L-proline methyl ester|CS-W001497

Structure of 203866-17-5

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General Information

  • CAS No. 203866-17-5
  • Cat. No. CS-W001497
  • Purity ≥98%
  • MDL No. MFCD03094918
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₁H₁₇F₂NO₄
  • Molecular Weight 265.25
  • Synonym(s) 1,2-pyrrolidinedicarboxylic acid, 4,4-difluoro-, 1-(1,1-dimethylethyl) 2-methyl ester, (2S)-
  • SMILES COC(=O)[C@@H]1CC(CN1C(=O)OC(C)(C)C)(F)F

Description

N-Boc-4,4-difluoro-L-proline methyl ester features a sterically constrained proline scaffold with dual fluorine atoms at the C4 position, enhancing conformational rigidity and metabolic stability. The Boc-protected amine and methyl ester functionality enable straightforward incorporation into peptide chains, facilitating efficient synthesis of fluorinated peptidomimetics under standard coupling conditions.

Application

N-Boc-4,4-difluoro-L-proline methyl ester serves as a conformationally constrained building block for peptide synthesis, leveraging the stereoelectronic effects of geminal difluorination to stabilize the Cγ-exo pseudoproline turn. The Boc group ensures stability and orthogonal deprotection, while the methyl ester facilitates downstream transformations. This derivative enables efficient incorporation into peptidomimetics and bioactive scaffolds, offering enhanced metabolic stability and defined backbone geometry in synthetic sequences.

Synthesis

  • Route1

    References

    • ADDEX PHARMACEUTICALS SA Patent: WO2006/123257 A2, 2006 ; Location in patent: Page/Page column 70 ; WO 2006/123257 A2
  • Route2

    References

    • Tetrahedron Letters, , vol. 44, # 42 p. 7809 - 7812
  • Route3

    References

    • Tetrahedron Letters, , vol. 44, # 42 p. 7809 - 7812

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

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Computational Chemistry Data

  • TPSA   55.84
  • LogP   1.8041
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   1

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