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(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-2-cyclopentylacetic acid

  • CAS No. 187475-29-2

  • Cat. No. CS-0089981
  • Purity≥98%
  • MDL No.None

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

(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-2-cyclopentylacetic acid|CS-0089981

Structure of 187475-29-2

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General Information

  • CAS No. 187475-29-2
  • Cat. No. CS-0089981
  • Purity ≥98%
  • MDL No. None
  • Storage -20°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₂₃H₂₅NO₄
  • Molecular Weight 379.45
  • Synonym(s) Fmoc-(S)-N-methylcyclopentylglycine
  • SMILES O=C(O)[C@@H](N(C(OCC1C2=C(C3=C1C=CC=C3)C=CC=C2)=O)C)C4CCCC4

Description

This chiral building block features a fluorenylmethoxycarbonyl (Fmoc)-protected amine and a cyclopentyl-substituted acetic acid moiety, enabling direct incorporation into peptide chains. The stereochemistry at the α-carbon ensures high diastereoselectivity in coupling reactions, while the Fmoc group provides orthogonal protection for amine-directed synthesis.

Application

(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-2-cyclopentylacetic acid serves as a robust chiral building block for peptide synthesis, enabling efficient incorporation of sterically hindered, non-proteinogenic amino acid motifs. The Fmoc group provides excellent stability and orthogonal deprotection, while the methylamino and cyclopentyl functionalities offer defined stereochemical control and enhanced lipophilicity—ideal for medicinal chemistry campaigns requiring tailored scaffold diversity.

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+P364-P405-P501

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Computational Chemistry Data

  • TPSA   66.84
  • LogP   4.5107
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   5

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