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CS-W001157 4
Total: USD 88.00

2-((tert-Butyldiphenylsilyl)oxy)acetic acid

  • CAS No. 76271-74-4

  • Cat. No. CS-W021372
  • Purity≥95%
  • MDL No.MFCD20039760

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

2-((tert-Butyldiphenylsilyl)oxy)acetic acid|CS-W021372

Structure of 76271-74-4

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General Information

  • CAS No. 76271-74-4
  • Cat. No. CS-W021372
  • Purity ≥95%
  • MDL No. MFCD20039760
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₈H₂₂O₃Si
  • Molecular Weight 314.45
  • Synonym(s) 2-((tert-Butyldiphenylsilyl)oxy)
  • SMILES CC(C)(C)[Si](OCC(O)=O)(C1=CC=CC=C1)C1=CC=CC=C1

Description

This silyl-protected acetic acid derivative features a tert-butyldiphenylsilyl group that confers exceptional stability and solubility in organic media. The pendant hydroxyl moiety enables selective derivatization, while the robust silyl protection resists moisture and acidic conditions. Ideal for orthogonal functionalization in complex molecule synthesis.

Application

2-((tert-Butyldiphenylsilyl)oxy)acetic acid serves as a robust protecting group for carboxylic acids, enabling orthogonal protection in complex molecule synthesis. Its tert-butyldiphenylsilyl (TBS) moiety provides excellent stability under a wide range of reaction conditions, while the acetic acid functionality allows for selective derivatization. The compound facilitates efficient purification and is compatible with standard deprotection protocols, making it a practical choice for multi-step synthetic sequences involving sensitive functional groups.

Synthesis

  • Route1
    • Methyl 2-((tert-butyldiphenylsilyl)oxy)acetate|CS-0337075
      154698-92-7
    • ~94%
    • In-stock
      2-((tert-Butyldiphenylsilyl)oxy)acetic acid|CS-W021372
      76271-74-4

    References

    • Ascenso, Osvaldo S.; Marques, Joao C.; Santos, Ana Rita; Xavier, Karina B.; Rita Ventura; Maycock, Christopher D. Bioorganic and Medicinal Chemistry, 2011 , vol. 19, # 3 p. 1236 - 1241
  • Route2
    • In-stock
      Glycolic acid|CS-W016683
      79-14-1
    • null|null
      58479-61-1
    • ~79%
    • In-stock
      2-((tert-Butyldiphenylsilyl)oxy)acetic acid|CS-W021372
      76271-74-4

    References

    • Nicolaou; Snyder, Scott A.; Huang, Xianhai; Simonsen, Klaus B.; Koumbis, Alexandros E.; Bigot, Antony Journal of the American Chemical Society, 2004 , vol. 126, # 32 p. 10162 - 10173
  • Route3
    • null|null
      139888-79-2
    • ~87%
    • In-stock
      2-((tert-Butyldiphenylsilyl)oxy)acetic acid|CS-W021372
      76271-74-4

    References

    • Fanjul, Sandra; Hulme, Alison N. Journal of Organic Chemistry, 2008 , vol. 73, # 24 p. 9788 - 9791

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   46.53
  • LogP   2.6476
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   5

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