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CS-W001157 4
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(S)-3-((tert-Butoxycarbonyl)amino)-2-hydroxypropanoic acid

  • CAS No. 52558-24-4

  • Cat. No. CS-W021169
  • Purity≥97%
  • MDL No.MFCD17011798

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

(S)-3-((tert-Butoxycarbonyl)amino)-2-hydroxypropanoic acid|CS-W021169

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General Information

  • CAS No. 52558-24-4
  • Cat. No. CS-W021169
  • Purity ≥97%
  • MDL No. MFCD17011798
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₁₅NO₅
  • Molecular Weight 205.21
  • Synonym(s) Propanoic acid, 3-[[(1,1-dimethylethoxy)carbonyl]amino]-2-hydroxy-, (2S)-
  • SMILES O=C(O)[C@@H](O)CNC(OC(C)(C)C)=O

Description

This chiral building block features a protected amino group and a hydroxyl-bearing carbon, enabling direct incorporation into peptide syntheses. The tert-butoxycarbonyl (Boc) moiety provides stability under basic conditions, while the hydroxypropanoic acid scaffold offers a handle for derivatization. This configuration supports stereocontrolled assembly of complex bioactive molecules in medicinal chemistry workflows.

Application

(S)-3-((tert-Butoxycarbonyl)amino)-2-hydroxypropanoic acid serves as a stable, bench-ready chiral building block for peptide synthesis and medicinal chemistry. The Boc-protected amine enables orthogonal deprotection in standard workflows, while the β-hydroxy carboxylic acid functionality facilitates stereoselective transformations and incorporation into heterocyclic scaffolds. Its robust stability under ambient conditions and ease of purification make it ideal for multi-step syntheses requiring high reproducibility.

Synthesis

  • Route1

    References

    • Yang, Kanghui; Fen, Jinghong; Fang, Hao; Zhang, Lei; Gong, Jianzhi; Xu, Wenfang Journal of Enzyme Inhibition and Medicinal Chemistry, 2012 , vol. 27, # 2 p. 302 - 310
  • Route2

    References

    • ACHAOGEN, INC.; AGGEN, James, Bradley; LINSELL, Martin, Sheringham; GOLDBLUM, Adam, Aaron; HILDEBRANDT, Darin, James; KANE, Timothy, Robert; DOZZO, Paola; GLIEDT, Micah, James; MOSER, Heinz, Ernst Patent: WO2010/42850 A1, 2010 ; Location in patent: Page/Page column 55-56 ; WO 2010/042850 A1
  • Route3
    • null|null
      169688-48-6
    • ~75%
    • In-stock
      (S)-3-((tert-Butoxycarbonyl)amino)-2-hydroxypropanoic acid|CS-W021169
      52558-24-4

    References

    • Andruszkiewicz, Ryszard; Wyszogrodzka, Monika Synlett, 2002 , # 12 p. 2101 - 2103

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   95.86
  • LogP   -0.0434
  • H_Acceptors   4
  • H_Donors   3
  • Rotatable_Bonds   3

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