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CS-W001157 4
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1,3-Bis(benzyloxycarbonyl)-2-methyl-2-thiopseudourea

  • CAS No. 25508-20-7

  • Cat. No. CS-0199060
  • Purity≥97%
  • MDL No.None

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

1,3-Bis(benzyloxycarbonyl)-2-methyl-2-thiopseudourea|CS-0199060

Structure of 25508-20-7

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General Information

  • CAS No. 25508-20-7
  • Cat. No. CS-0199060
  • Purity ≥97%
  • MDL No. None
  • Storage 4°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₈H₁₈N₂O₄S
  • Molecular Weight 358.41
  • Synonym(s) dibenzyl [(methylsulfanyl)methylylidene]biscarbamate
  • SMILES O=C(OCC1=CC=CC=C1)N=C(SC)NC(OCC2=CC=CC=C2)=O

Description

1,3-Bis(benzyloxycarbonyl)-2-methyl-2-thiopseudourea features a sterically hindered thiourea core flanked by two benzyloxycarbonyl groups, enabling stable incorporation into peptide-based scaffolds. This derivative delivers enhanced solubility and protection for cysteine mimics during synthetic workflows.

Application

1,3-Bis(benzyloxycarbonyl)-2-methyl-2-thiopseudourea serves as a versatile thiourea-based building block for the synthesis of sulfur-containing heterocycles and peptide mimetics. Its benzyloxycarbonyl groups provide orthogonal protection for nitrogen functionalities, enabling sequential deprotection and functionalization. The molecule exhibits bench stability, facilitates efficient purification via chromatography, and participates reliably in standard coupling reactions, making it well-suited for medicinal chemistry and solid-phase synthesis workflows.

Synthesis

  • Route1
    • In-stock
      S-Methylisothiourea sulfate|CS-0011749
      867-44-7
    • null|null
      501-53-1
    • ~98%
    • In-stock
      1,3-Bis(benzyloxycarbonyl)-2-methyl-2-thiopseudourea|CS-0199060
      25508-20-7

    References

    • Lal, Bansi; Gangopadhyay Tetrahedron Letters, 1996 , vol. 37, # 14 p. 2483 - 2486
  • Route2

    References

    • Gers, Tomasz; Kunce, Danuta; Markowski, Pawel; Izdebski, Jan Synthesis, 2004 , # 1 p. 37 - 42
  • Route3

    References

    • Gers, Tomasz; Kunce, Danuta; Markowski, Pawel; Izdebski, Jan Synthesis, 2004 , # 1 p. 37 - 42

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

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Computational Chemistry Data

  • TPSA   76.99
  • LogP   3.9686
  • H_Acceptors   5
  • H_Donors   1
  • Rotatable_Bonds   4

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