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CS-W001157 4
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(S)-Methyl 2-((tert-butoxycarbonyl)amino)-3-methylbutanoate

  • CAS No. 58561-04-9

  • Cat. No. CS-W008593
  • Purity≥97%
  • MDL No.MFCD00672510

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

(S)-Methyl 2-((tert-butoxycarbonyl)amino)-3-methylbutanoate|CS-W008593

Structure of 58561-04-9

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General Information

  • CAS No. 58561-04-9
  • Cat. No. CS-W008593
  • Purity ≥97%
  • MDL No. MFCD00672510
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₁H₂₁NO₄
  • Molecular Weight 231.29
  • Synonym(s) None
  • SMILES O=C(OC)[C@H](C(C)C)NC(OC(C)(C)C)=O

Description

(S)-Methyl 2-((tert-butoxycarbonyl)amino)-3-methylbutanoate is a chiral building block featuring a sterically hindered side chain and a bench-stable Boc-protected amine. This configuration supports efficient incorporation into peptide synthesis, enabling direct coupling without racemization. The methyl ester facilitates downstream transformations under standard conditions.

Application

(S)-Methyl 2-((tert-butoxycarbonyl)amino)-3-methylbutanoate serves as a versatile chiral building block in peptide synthesis and medicinal chemistry. The Boc-protected amino group enables orthogonal handling, while the methyl ester facilitates downstream transformations. Its stability under standard reaction conditions and compatibility with diverse coupling protocols make it ideal for constructing complex scaffolds and peptidomimetics.

Synthesis

  • Route1

    References

    • Chemistry - A European Journal, , vol. 11, # 1 p. 69 - 80
  • Route2

    References

    • Chemical Communications, , vol. 50, # 13 p. 1588 - 1590
  • Route3
    • null|null
      67-56-1
    • In-stock
      Boc-L-Valine|CS-W002300
      13734-41-3
    • ~97%
    • In-stock
      (S)-Methyl 2-((tert-butoxycarbonyl)amino)-3-methylbutanoate|CS-W008593
      58561-04-9

    References

    • Chemical Communications, , vol. 46, # 17 p. 2947 - 2949

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

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Computational Chemistry Data

  • TPSA   64.63
  • LogP   1.7087
  • H_Acceptors   4
  • H_Donors   1
  • Rotatable_Bonds   3

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