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Dimethyl (2S,4R)-2-((tert-butoxycarbonyl)amino)-4-(cyanomethyl)pentanedioate

  • CAS No. 328086-57-3

  • Cat. No. CS-0131839
  • Molecule weight314.33
  • Purity≥95%
  • MDL No.MFCD28138265

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

Dimethyl (2S,4R)-2-((tert-butoxycarbonyl)amino)-4-(cyanomethyl)pentanedioate|CS-0131839

Structure of 328086-57-3

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General Information

  • CAS No. 328086-57-3
  • Cat. No. CS-0131839
  • Purity ≥95%
  • MDL No. MFCD28138265
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₄H₂₂N₂O₆
  • Molecular Weight 314.33
  • Synonym(s) None
  • SMILES O=C(OC)[C@@H](CC#N)C[C@@H](C(OC)=O)NC(OC(C)(C)C)=O

Description

Dimethyl (2S,4R)-2-((tert-butoxycarbonyl)amino)-4-(cyanomethyl)pentanedioate features a chiral diester scaffold with a protected amino group and a nitrile-bearing side chain. This configuration enables selective coupling in peptide synthesis, where the tert-butyl carbamate provides orthogonal protection and the cyanomethyl handle facilitates downstream functionalization. The molecule exhibits excellent stability under standard bench conditions.

Application

Dimethyl (2S,4R)-2-((tert-butoxycarbonyl)amino)-4-(cyanomethyl)pentanedioate serves as a versatile chiral building block for the synthesis of peptidomimetics and heterocyclic scaffolds. Its pendant nitrile group enables efficient transformations to amides, carboxylic acids, or cyclic derivatives, while the protected α-amino functionality supports sequential coupling and deprotection strategies. The molecule exhibits excellent bench stability and facilitates straightforward purification, making it well-suited for iterative synthesis in medicinal chemistry workflows.

Safety Information

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GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H302-H315-H319
Precautionary Statements : P264-P270-P280-P302+P352-P330-P362+P364-P501

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Computational Chemistry Data

  • TPSA   114.72
  • LogP   1.14568
  • H_Acceptors   7
  • H_Donors   1
  • Rotatable_Bonds   6

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