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CS-W001157 4
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(S)-Methyl 2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(4-hydroxyphenyl)propanoate

  • CAS No. 82911-79-3

  • Cat. No. CS-0040950
  • Molecule weight417.45
  • Purity≥98%
  • MDL No.MFCD11044348

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

(S)-Methyl 2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(4-hydroxyphenyl)propanoate|CS-0040950

Structure of 82911-79-3

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General Information

  • CAS No. 82911-79-3
  • Cat. No. CS-0040950
  • Purity ≥98%
  • MDL No. MFCD11044348
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₂₅H₂₃NO₅
  • Molecular Weight 417.45
  • Synonym(s) Fmoc-Tyr-Ome
  • SMILES OC(C=C1)=CC=C1C[C@@H](C(OC)=O)NC(OCC2C3=C(C4=C2C=CC=C4)C=CC=C3)=O

Description

(S)-Methyl 2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(4-hydroxyphenyl)propanoate is a chiral building block featuring a fluorenylmethoxycarbonyl (Fmoc) protected amino group and a phenolic hydroxyl. This combination enables orthogonal functionalization in peptide synthesis and conjugation workflows, where the Fmoc moiety facilitates selective deprotection under mild basic conditions. The molecule's stability under standard bench protocols supports reliable handling during iterative coupling steps.

Application

(S)-Methyl 2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(4-hydroxyphenyl)propanoate serves as a key chiral building block for the synthesis of peptide-like scaffolds and bioactive molecules. The Fmoc group enables efficient orthogonal protection during solid-phase synthesis, while the pendant phenolic hydroxyl supports further derivatization via etherification or oxidation. Bench-stable and readily purified by flash chromatography, it facilitates reliable incorporation into complex intermediates for medicinal chemistry applications.

Synthesis

  • Route1

    References

    • Adamson, J. Gordon; Blaskovich, Mark A.; Groenevelt, Hester; Lajoie, Gilles A. Journal of Organic Chemistry, 1991 , vol. 56, # 10 p. 3447 - 3449
  • Route2
    • null|null
      845786-39-2
    • ~92%
    • In-stock
      (S)-Methyl 2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(4-hydroxyphenyl)propanoate|CS-0040950
      82911-79-3

    References

    • Gerstenberger, Brian S.; Konopelski, Joseph P. Journal of Organic Chemistry, 2005 , vol. 70, # 4 p. 1467 - 1470
  • Route3
    • null|null
      28920-43-6
    • In-stock
      H-Tyr-OMe.HCl|CS-W012944
      3417-91-2
    • ~%
    • In-stock
      (S)-Methyl 2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(4-hydroxyphenyl)propanoate|CS-0040950
      82911-79-3

    References

    • Maryanoff, Bruce E.; Greco, Michael N.; Zhang, Han-Cheng; Andrade-Gordon, Patricia; Kauffman, Jack A.; Nicolaou; Liu, Aijun; Brungs, Peter H. Journal of the American Chemical Society, 1995 , vol. 117, # 4 p. 1225 - 1239

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

Quality Control

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Computational Chemistry Data

  • TPSA   84.86
  • LogP   4.015
  • H_Acceptors   5
  • H_Donors   2
  • Rotatable_Bonds   6

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