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CS-W001157 4
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N-(tert-Butoxycarbonyl)-N-methyl-D-leucine

  • CAS No. 89536-84-5

  • Cat. No. CS-W010251
  • Purity≥97%
  • MDL No.MFCD00076953

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

N-(tert-Butoxycarbonyl)-N-methyl-D-leucine|CS-W010251

Structure of 89536-84-5

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General Information

  • CAS No. 89536-84-5
  • Cat. No. CS-W010251
  • Purity ≥97%
  • MDL No. MFCD00076953
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₂H₂₃NO₄
  • Molecular Weight 245.32
  • Synonym(s) None
  • SMILES CC(C)C[C@H](C(O)=O)N(C(OC(C)(C)C)=O)C

Description

N-(tert-Butoxycarbonyl)-N-methyl-D-leucine features a sterically hindered tert-butyl carbamate protecting group and a methylated nitrogen, enabling stable incorporation into peptide sequences. This D-amino acid derivative supports efficient synthesis of non-natural peptides with enhanced metabolic stability and resistance to proteolytic degradation under standard conditions.

Application

N-(tert-Butoxycarbonyl)-N-methyl-D-leucine serves as a robust chiral building block for peptide synthesis, offering enhanced stability and orthogonal protection. The Boc group enables mild acidic deprotection, while the N-methyl substitution reduces amide hydrogen bonding, improving solubility and membrane permeability in peptidomimetic applications. Its D-leucine backbone provides stereochemical control in constrained peptide architectures, facilitating efficient coupling and purification in standard solid-phase workflows.

Synthesis

  • Route1
    • In-stock
      (tert-Butoxycarbonyl)-D-leucine|CS-0010908
      16937-99-8
    • null|null
      74-88-4
    • ~%
    • In-stock
      N-(tert-Butoxycarbonyl)-N-methyl-D-leucine|CS-W010251
      89536-84-5

    References

    • Journal of the American Chemical Society, , vol. 111, # 2 p. 669 - 673

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   66.84
  • LogP   2.3526
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   4

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