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CS-W001157 4
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(S)-2-((tert-Butoxycarbonyl)amino)-4,4-difluorobutanoic acid

  • CAS No. 467442-20-2

  • Cat. No. CS-0134029
  • Purity≥97%
  • MDL No.MFCD12755805

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

(S)-2-((tert-Butoxycarbonyl)amino)-4,4-difluorobutanoic acid|CS-0134029

Structure of 467442-20-2

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General Information

  • CAS No. 467442-20-2
  • Cat. No. CS-0134029
  • Purity ≥97%
  • MDL No. MFCD12755805
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₁₅F₂NO₄
  • Molecular Weight None
  • Synonym(s) (S)-2-(Tert-butoxycarbonylamino)-4,4-difluorobutanoic acid
  • SMILES O=C(O)[C@@H](NC(OC(C)(C)C)=O)CC(F)F

Description

(S)-2-((tert-Butoxycarbonyl)amino)-4,4-difluorobutanoic acid is a chiral building block featuring a sterically hindered difluoromethylene group and a bench-stable Boc-protected amine. This configuration enables direct incorporation into peptide sequences requiring fluorinated aliphatic side chains, offering enhanced metabolic stability and controlled conformational rigidity in synthetic bioactive molecules.

Application

(S)-2-((tert-Butoxycarbonyl)amino)-4,4-difluorobutanoic acid serves as a stable, bench-ready building block for the synthesis of fluorinated peptide mimetics and bioactive heterocycles. The Boc-protected amine and difluoromethylene group enable orthogonal functionalization and enhanced metabolic stability. Its well-defined stereochemistry and compatibility with standard coupling conditions facilitate reliable incorporation into complex scaffolds.

Synthesis

  • Route1

    References

    • Bioorganic and medicinal chemistry letters, , vol. 14, # 1 p. 239 - 243

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 : H315-H319-H335
Precautionary Statements : P260-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   75.63
  • LogP   1.6195
  • H_Acceptors   3
  • H_Donors   2
  • Rotatable_Bonds   4

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