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CS-W001157 4
Total: USD 88.00

Methyl ((benzyloxy)carbonyl)-D-serinate

  • CAS No. 93204-36-5

  • Cat. No. CS-0045089
  • Purity≥98%
  • MDL No.MFCD00799501

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

Methyl ((benzyloxy)carbonyl)-D-serinate|CS-0045089

Structure of 93204-36-5

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General Information

  • CAS No. 93204-36-5
  • Cat. No. CS-0045089
  • Purity ≥98%
  • MDL No. MFCD00799501
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₂H₁₅NO₅
  • Molecular Weight 253.25
  • Synonym(s) None
  • SMILES O=C(OC)[C@H](NC(OCC1=CC=CC=C1)=O)CO

Description

Methyl ((benzyloxy)carbonyl)-D-serinate is a protected D-serine derivative featuring a labile benzyl ester and a robust carbobenzoxy (Cbz) amine group. This bifunctional scaffold enables selective peptide chain elongation in synthetic workflows, where the Cbz moiety offers stability under standard conditions while the methyl ester facilitates controlled deprotection. The compound integrates seamlessly into solid-phase synthesis protocols for bioactive peptide analogs.

Application

Methyl ((benzyloxy)carbonyl)-D-serinate serves as a key chiral building block in peptide synthesis, offering a protected D-serine derivative with orthogonal functionality. The benzyloxycarbonyl (Cbz) group provides stable protection under standard coupling conditions, while the methyl ester facilitates straightforward hydrolysis and derivatization. Its bench-stable nature and compatibility with common amide bond formation protocols enable efficient incorporation into complex peptide scaffolds.

Synthesis

  • Route1
    • In-stock
      H-D-Ser-OMe.HCl|CS-W016249
      5874-57-7
    • null|null
      501-53-1
    • ~97%
    • In-stock
      Methyl ((benzyloxy)carbonyl)-D-serinate|CS-0045089
      93204-36-5

    References

    • Martin, Nathaniel I.; Woodward, Joshua J.; Winter, Michael B.; Marletta, Michael A. Bioorganic and Medicinal Chemistry Letters, 2009 , vol. 19, # 6 p. 1758 - 1762
  • Route2
    • Methyl serinate|CS-0449843
      2104-89-4
    • null|null
      501-53-1
    • ~94%
    • In-stock
      Methyl ((benzyloxy)carbonyl)-D-serinate|CS-0045089
      93204-36-5

    References

    • Zhao; Qiao; Rong; Kozikowski Tetrahedron Letters, 2000 , vol. 41, # 45 p. 8711 - 8715
  • Route3
    • null|null
      67-56-1
    • null|null
      503071-00-9
    • ~99%
    • In-stock
      Methyl ((benzyloxy)carbonyl)-D-serinate|CS-0045089
      93204-36-5

    References

    • Panunzio, Mauro; Bandini, Elisa; Campana, Eileen; Vicennati, Paola Tetrahedron Asymmetry, 2002 , vol. 13, # 19 p. 2113 - 2115

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-P330-P362+P364-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   84.86
  • LogP   0.4467
  • H_Acceptors   5
  • H_Donors   2
  • Rotatable_Bonds   5

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