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CS-W001157 4
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(2S)-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-4,4-difluoro-Butanoic acid

  • CAS No. 467442-21-3

  • Cat. No. CS-0029895
  • Purity≥98%
  • MDL No.MFCD06796145

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

(2S)-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-4,4-difluoro-Butanoic acid|CS-0029895

Structure of 467442-21-3

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General Information

  • CAS No. 467442-21-3
  • Cat. No. CS-0029895
  • Purity ≥98%
  • MDL No. MFCD06796145
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₉H₁₇F₂NO₄
  • Molecular Weight 361.34
  • Synonym(s) (S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-4,4-difluoro-butyric acid
  • SMILES O=C(O)[C@@H](NC(OCC1C2=C(C3=C1C=CC=C3)C=CC=C2)=O)CC(F)F

Description

This fluorenylmethoxycarbonyl-protected amino acid derivative features a sterically hindered, electron-deficient difluorobutanoic acid backbone. Designed for efficient peptide synthesis, the Fmoc group enables orthogonal deprotection while the geminal difluoro substitution enhances metabolic stability and modulates conformational preferences in folded peptides.

Application

(2S)-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-4,4-difluoro-butanoic acid serves as a valuable chiral building block for peptide synthesis, enabling the incorporation of sterically constrained, electron-deficient amino acid surrogates. The fluorenylmethoxycarbonyl (Fmoc) group provides orthogonal protection with excellent stability and ease of removal under mild basic conditions. The 4,4-difluoro substitution enhances metabolic stability and modulates backbone conformation, facilitating the construction of bioactive peptidomimetics and heterocyclic scaffolds in medicinal chemistry campaigns.

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-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   75.63
  • LogP   3.6335
  • H_Acceptors   3
  • H_Donors   2
  • Rotatable_Bonds   6

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