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CS-W001157 4
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5-((tert-Butyldimethylsilyl)oxy)pentanoic acid

  • CAS No. 87729-39-3

  • Cat. No. CS-0376640
  • Purity≥95%
  • MDL No.None

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

5-((tert-Butyldimethylsilyl)oxy)pentanoic acid|CS-0376640

Structure of 87729-39-3

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General Information

  • CAS No. 87729-39-3
  • Cat. No. CS-0376640
  • Purity ≥95%
  • MDL No. None
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₁H₂₄O₃Si
  • Molecular Weight 232.40
  • Synonym(s) None
  • SMILES O=C(O)CCCCO[Si](C)(C)C(C)(C)C

Description

5-((tert-Butyldimethylsilyl)oxy)pentanoic acid offers a protected hydroxyl group flanked by a carboxylic acid, enabling orthogonal functionalization in complex molecule synthesis. The silyl ether confers enhanced stability and moisture tolerance, facilitating handling under standard conditions. This derivative integrates seamlessly into peptide and natural product workflows where selective protection is critical.

Application

5-((tert-Butyldimethylsilyl)oxy)pentanoic acid serves as a stable, bench-friendly protecting group for carboxylic acids and hydroxyl functionalities, enabling orthogonal protection in complex molecule synthesis. The silyl ether moiety offers excellent stability under basic conditions and mild acidic deprotection, facilitating sequential functionalization. This compound functions as a key building block in the synthesis of polyfunctional intermediates, particularly in natural product and pharmaceutical scaffolds requiring selective reactivity.

Synthesis

  • Route1

    References

    • Takemoto; Yasuda; Ley Synlett, 2001 , # 10 p. 1555 - 1556
  • Route2
    • null|null
      87729-38-2
    • ~80%
    • In-stock
      5-((tert-Butyldimethylsilyl)oxy)pentanoic acid|CS-0376640
      87729-39-3

    References

    • Trost, Barry M.; McDougal, Patrick G. Journal of Organic Chemistry, 1984 , vol. 49, # 3 p. 458 - 468
  • Route3

    References

    • Trost, Barry M.; McDougal, Patrick G. Journal of Organic Chemistry, 1984 , vol. 49, # 3 p. 458 - 468

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   3.2631
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   6

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