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CS-W001157 4
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2-(((Benzyloxy)carbonyl)amino)-3-hydroxypropanoic acid

  • CAS No. 2768-56-1

  • Cat. No. CS-0059139
  • Purity≥98%
  • MDL No.MFCD00063143

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

2-(((Benzyloxy)carbonyl)amino)-3-hydroxypropanoic acid|CS-0059139

Structure of 2768-56-1

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General Information

  • CAS No. 2768-56-1
  • Cat. No. CS-0059139
  • Purity ≥98%
  • MDL No. MFCD00063143
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₁H₁₃NO₅
  • Molecular Weight 239.22
  • Synonym(s) None
  • SMILES OCC(C(O)=O)NC(OCC1=CC=CC=C1)=O

Description

This hydroxylated amino acid derivative features a benzyl-protected amine and a reactive carboxylic acid group, enabling straightforward incorporation into peptide synthesis. The benzyloxy carbonyl moiety provides stable protection under standard conditions, while the 3-hydroxy functionality offers a handle for further derivatization or conjugation in bioconjugate applications.

Application

2-(((Benzyloxy)carbonyl)amino)-3-hydroxypropanoic acid serves as a versatile building block in peptide synthesis and medicinal chemistry, enabling the introduction of hydroxylated amino acid motifs with orthogonal protection. The benzyloxycarbonyl (Boc) group provides stable nitrogen protection compatible with standard deprotection conditions, while the pendant hydroxyl and carboxylic acid functionalities offer sites for further derivatization. Its bench-stable nature and clean reaction profile facilitate efficient incorporation into complex molecular architectures.

Synthesis

  • Route1
    • In-stock
      DL-Serine|CS-0015292
      302-84-1
    • null|null
      501-53-1
    • ~82%
    • In-stock
      2-(((Benzyloxy)carbonyl)amino)-3-hydroxypropanoic acid|CS-0059139
      2768-56-1

    References

    • King, Amber M.; Salome, Christophe; Dinsmore, Jason; Salome-Grosjean, Elise; De Ryck, Marc; Kaminski, Rafal; Valade, Anne; Kohn, Harold Journal of Medicinal Chemistry, 2011 , vol. 54, # 13 p. 4815 - 4830
  • Route2
    • In-stock
      DL-Serine|CS-0015292
      302-84-1
    • null|null
      501-53-1
    • ~%
    • In-stock
      2-(((Benzyloxy)carbonyl)amino)-3-hydroxypropanoic acid|CS-0059139
      2768-56-1
    • null|null
      274689-81-5

    References

    • Levene; Schormueller Journal of Biological Chemistry, 1934 , vol. 105, p. 547,551
  • Route3

    References

    • Bergmann; Zervas Chemische Berichte, 1932 , vol. 65, p. 1192,1198

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   0.3583
  • H_Acceptors   4
  • H_Donors   3
  • Rotatable_Bonds   5

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