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CS-W001157 4
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Boc-L-Homoserine lactone

  • CAS No. 40856-59-5

  • Cat. No. CS-W018939
  • Purity≥97%
  • MDL No.MFCD04973958

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

Boc-L-Homoserine lactone|CS-W018939

Structure of 40856-59-5

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General Information

  • CAS No. 40856-59-5
  • Cat. No. CS-W018939
  • Purity ≥97%
  • MDL No. MFCD04973958
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₁₅NO₄
  • Molecular Weight 201.22
  • Synonym(s) tert-Butyl [(3S)-2-oxotetrahydrofuran-3-yl]carbamate
  • SMILES CC(C)(C)OC(=O)N[C@H]1CCOC1=O

Description

Boc-L-Homoserine lactone features a protected hydroxyl-bearing amino acid scaffold with a stable cyclic ester core. This bench-stable derivative enables direct incorporation into peptide synthesis workflows without side-chain interference, offering reliable access to homoserine-containing sequences in biopharmaceutical and chemical biology applications.

Application

Boc-L-Homoserine lactone serves as a versatile building block in peptide and heterocyclic synthesis, enabling efficient access to β-lactone-containing scaffolds. Its bench-stable Boc protection offers excellent functional group tolerance, facilitating subsequent transformations such as ring-opening reactions and coupling protocols. Widely employed in medicinal chemistry campaigns, it functions as a key intermediate for constructing bioactive motifs and cyclic peptide analogs with predictable reactivity under standard conditions.

Synthesis

  • Route1

    References

    • Stachel; Chul Bom Lee; Spassova; Chappell; Bornmann; Danishefsky; Chou; Guan Journal of Organic Chemistry, 2001 , vol. 66, # 12 p. 4369 - 4378
  • Route2
    • In-stock
      Di-tert-butyl dicarbonate|CS-0017817
      24424-99-5
    • 3-Aminooxolan-2-one hydrobromide|CS-0039961
      6305-38-0
    • ~98%
    • In-stock
      Boc-L-Homoserine lactone|CS-W018939
      40856-59-5

    References

    • Biel, Markus; Deck, Patrick; Giannis, Athanassios; Waldmann, Herbert Chemistry - A European Journal, 2006 , vol. 12, # 15 p. 4121 - 4143
  • Route3

    References

    • De Jonghe, Steven; Lamote, Inge; Venkataraman, Krishnan; Boldin, Swetlana A.; Hillaert, Ulrik; Rozenski, Jef; Hendrix, Chris; Busson, Roger; De Keukeleire, Denis; Van Calenbergh, Serge; Futerman, Anthony H.; Herdewijn, Piet Journal of Organic Chemistry, 2002 , vol. 67, # 3 p. 988 - 996

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   64.63
  • LogP   0.8266
  • H_Acceptors   4
  • H_Donors   1
  • Rotatable_Bonds   1

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