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(S)-3-(tert-Butoxycarbonyl)-2,2-dimethyloxazolidine-4-carboxylic acid

  • CAS No. 139009-66-8

  • Cat. No. CS-0102792
  • Molecule weight245.27
  • Purity≥95%
  • MDL No.MFCD02682656

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

(S)-3-(tert-Butoxycarbonyl)-2,2-dimethyloxazolidine-4-carboxylic acid|CS-0102792

Structure of 139009-66-8

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General Information

  • CAS No. 139009-66-8
  • Cat. No. CS-0102792
  • Purity ≥95%
  • MDL No. MFCD02682656
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₁H₁₉NO₅
  • Molecular Weight 245.27
  • Synonym(s) (S)-N-Boc-2,2-dimethyloxazolidine-4-carboxylic Acid
  • SMILES O=C(N1C(C)(C)OC[C@H]1C(O)=O)OC(C)(C)C

Description

(S)-3-(tert-Butoxycarbonyl)-2,2-dimethyloxazolidine-4-carboxylic acid is a chiral building block featuring a sterically hindered oxazolidine core and a protected carboxylic acid. This bench-stable derivative enables direct incorporation into peptide synthesis workflows, offering enhanced stability during handling and purification. The tert-butoxycarbonyl group facilitates selective deprotection under mild acidic conditions, streamlining downstream functionalization.

Application

(S)-3-(tert-Butoxycarbonyl)-2,2-dimethyloxazolidine-4-carboxylic acid serves as a robust chiral synthon in peptide and heterocycle synthesis, enabling stereoselective C–N bond formation. The protected oxazolidine moiety offers excellent bench stability and facilitates efficient deprotection under mild acidic conditions. Its functional group tolerance supports diverse transformations, including coupling reactions and nucleophilic additions, making it a reliable building block for complex molecular architectures.

Synthesis

  • Route1

    References

    • UCB PHARMA S.A. Patent: WO2008/128919 A2, 2008 ; Location in patent: Page/Page column 56 ; WO 2008/128919 A2
  • Route2
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      (S)-3-(tert-Butoxycarbonyl)-2,2-dimethyloxazolidine-4-carboxylic acid|CS-0102792
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    References

    • Lin, Chun-Chieh; Tantisantisom, Worawan; McAlpine, Shelli R. Organic Letters, 2013 , vol. 15, # 14 p. 3574 - 3577
  • Route3

    References

    • Hoffman, Robert V.; Tao, Junhua Tetrahedron Letters, 1998 , vol. 39, # 23 p. 3953 - 3956

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-P280-P302+P352

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Computational Chemistry Data

  • TPSA   76.07
  • LogP   1.443
  • H_Acceptors   4
  • H_Donors   1
  • Rotatable_Bonds   1

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