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CS-W001157 4
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O-Benzyl-N-(tert-butoxycarbonyl)-L-homoserine

  • CAS No. 59408-74-1

  • Cat. No. CS-0127682
  • Molecule weight309.36
  • Purity≥97%
  • MDL No.MFCD00270497

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

O-Benzyl-N-(tert-butoxycarbonyl)-L-homoserine|CS-0127682

Structure of 59408-74-1

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General Information

  • CAS No. 59408-74-1
  • Cat. No. CS-0127682
  • Purity ≥97%
  • MDL No. MFCD00270497
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₆H₂₃NO₅
  • Molecular Weight 309.36
  • Synonym(s) N-Alpha-t-Butyloxy-O-Benzyl-L-Homoserine
  • SMILES O=C(O)[C@H](CCOCC1=CC=CC=C1)NC(OC(C)(C)C)=O

Description

O-Benzyl-N-(tert-butoxycarbonyl)-L-homoserine features a protected hydroxyl group and a stable tert-butyl carbamate handle, enabling reliable incorporation into peptide sequences. This derivative delivers enhanced solubility and stability during solid-phase synthesis workflows, facilitating efficient chain elongation in complex peptide assembly.

Application

O-Benzyl-N-(tert-butoxycarbonyl)-L-homoserine serves as a versatile chiral building block in peptide and heterocycle synthesis, offering orthogonal protection for both hydroxyl and amine functionalities. The benzyl ether provides stable O-protection compatible with standard deprotection conditions, while the Boc group enables mild acid-labile N-protection. This combination facilitates sequential functionalization and purification under routine bench conditions, supporting efficient access to complex scaffolds in medicinal chemistry and natural product synthesis.

Synthesis

  • Route1
    • null|null
      1070-19-5
    • ~%
    • In-stock
      O-Benzyl-N-(tert-butoxycarbonyl)-L-homoserine|CS-0127682
      59408-74-1

    References

    • Justus Liebigs Annalen der Chemie, , p. 417 - 431
  • Route2
    • In-stock
      Boc-L-Homoserine|CS-W008113
      41088-86-2
    • null|null
      100-39-0
    • ~%
    • In-stock
      O-Benzyl-N-(tert-butoxycarbonyl)-L-homoserine|CS-0127682
      59408-74-1

    References

    • Justus Liebigs Annalen der Chemie, , p. 417 - 431

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

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Computational Chemistry Data

  • TPSA   84.86
  • LogP   2.5712
  • H_Acceptors   4
  • H_Donors   2
  • Rotatable_Bonds   7

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