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CS-W001157 4
Total: USD 88.00

Boc-Ser-OBzl

  • CAS No. 59524-02-6

  • Cat. No. CS-W009975
  • Purity≥98%
  • MDL No.MFCD00076983

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

Boc-Ser-OBzl|CS-W009975

Structure of 59524-02-6

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General Information

  • CAS No. 59524-02-6
  • Cat. No. CS-W009975
  • Purity ≥98%
  • MDL No. MFCD00076983
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₅H₂₁NO₅
  • Molecular Weight 295.33
  • Synonym(s) Boc-L-Serine benzyl ester
  • SMILES O=C([C@H](CO)NC(OC(C)(C)C)=O)OCC1=CC=CC=C1

Description

Boc-Ser-OBzl features a protected serine residue with orthogonal Boc and OBzl groups, enabling selective deprotection in peptide synthesis. This combination delivers enhanced stability during storage and handling, while the benzyl ester facilitates efficient cleavage under mild hydrogenolysis conditions.

Application

Boc-Ser-OBzl serves as a robust amino acid building block for peptide synthesis, offering orthogonal protection of both the α-amino and side-chain hydroxyl groups. The Boc group ensures stable amine protection under acidic conditions, while the benzyl ester facilitates selective deprotection during chain elongation. Its bench-stable nature and compatibility with standard coupling reagents enable efficient incorporation into complex sequences, particularly in the construction of serine-containing peptides and heterocyclic scaffolds requiring precise functional group management.

Synthesis

  • Route1
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      Di-tert-butyl dicarbonate|CS-0017817
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    • L-Serine benzyl ester benzenesulfonate salt|CS-0201872
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      Boc-Ser-OBzl|CS-W009975
      59524-02-6

    References

    • Stocking, Emily M.; Schwarz, Jessie N.; Senn, Hans; Salzmann, Michael; Silks, Louis A. Journal of the Chemical Society - Perkin Transactions 1, 1997 , # 16 p. 2443 - 2447
  • Route2
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      (S)-2-((tert-Butoxycarbonyl)amino)-3-hydroxypropanoic acid|CS-W015379
      3262-72-4
    • null|null
      100-39-0
    • ~99%
    • In-stock
      Boc-Ser-OBzl|CS-W009975
      59524-02-6

    References

    • UNIVERSITY OF VIRGINIA PATENT FOUNDATION Patent: WO2005/41899 A2, 2005 ; Location in patent: Page/Page column 94; 102-103 ; WO 2005/041899 A2
  • Route3
    • In-stock
      Di-tert-butyl dicarbonate|CS-0017817
      24424-99-5
    • L-Ser-OBzl|CS-0173542
      1738-72-3
    • ~95%
    • In-stock
      Boc-Ser-OBzl|CS-W009975
      59524-02-6

    References

    • Sowinski, Jennifer A.; Toogood, Peter L. Journal of Organic Chemistry, 1996 , vol. 61, # 22 p. 7671 - 7676

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   1.6154
  • H_Acceptors   5
  • H_Donors   2
  • Rotatable_Bonds   5

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