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tert-Butyl (2S)-2-hydroxy-3-methylbutanoate

  • CAS No. 3519-30-0

  • Cat. No. CS-B0164
  • Purity≥97%
  • MDL No.MFCD04972376

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

tert-Butyl (2S)-2-hydroxy-3-methylbutanoate|CS-B0164

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General Information

  • CAS No. 3519-30-0
  • Cat. No. CS-B0164
  • Purity ≥97%
  • MDL No. MFCD04972376
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₁₈O₃
  • Molecular Weight 174.24
  • Synonym(s) L-ALPHAHYDROXYISOVALERIC ACID T-BUTYL ESTER
  • SMILES O=C([C@@H](O)C(C)C)OC(C)(C)C

Description

tert-Butyl (2S)-2-hydroxy-3-methylbutanoate features a chiral hydroxyl-bearing side chain flanked by a tert-butyl ester group, enabling direct incorporation into asymmetric synthesis. The molecule exhibits enhanced stability under standard conditions and facilitates efficient derivatization in peptide and natural product assembly workflows.

Application

tert-Butyl (2S)-2-hydroxy-3-methylbutanoate serves as a chiral building block for synthesizing bioactive molecules, leveraging its stereogenic center and orthogonal functional groups. The tertiary butyl ester enables facile deprotection under mild acidic conditions, while the hydroxyl group supports selective derivatization via esterification or ether formation. This compound exhibits excellent bench stability and compatibility with standard synthetic workflows, facilitating efficient access to complex scaffolds in medicinal chemistry and natural product synthesis.

Synthesis

  • Route1
    • (S)-tert-butyl 2-acetoxy-3-methylbutanoate|CS-M0404
      380886-48-6
    • ~%
    • In-stock
      tert-Butyl (2S)-2-hydroxy-3-methylbutanoate|CS-B0164
      3519-30-0

    References

    • Bioorganic and Medicinal Chemistry Letters, , vol. 15, # 5 p. 1321 - 1326
  • Route2
    • null|null
      82301-82-4
    • ~75%
    • In-stock
      tert-Butyl (2S)-2-hydroxy-3-methylbutanoate|CS-B0164
      3519-30-0

    References

    • Kunz, H.; Bechtolsheimer, H.-H. Synthesis, 1982 , # 4 p. 303 - 304
  • Route3

    References

    • Bioorganic and Medicinal Chemistry, , vol. 14, # 12 p. 4260 - 4276

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   46.53
  • LogP   1.345
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   2

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