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CS-W001157 4
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(2S,4R)-1-(tert-Butoxycarbonyl)-4-((tert-butyldimethylsilyl)oxy)pyrrolidine-2-carboxylic acid

  • CAS No. 149814-40-4

  • Cat. No. CS-0047177
  • Purity≥97%
  • MDL No.None

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

(2S,4R)-1-(tert-Butoxycarbonyl)-4-((tert-butyldimethylsilyl)oxy)pyrrolidine-2-carboxylic acid|CS-0047177

Structure of 149814-40-4

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General Information

  • CAS No. 149814-40-4
  • Cat. No. CS-0047177
  • Purity ≥97%
  • MDL No. None
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₆H₃₁NO₅Si
  • Molecular Weight 345.51
  • Synonym(s) (4R)-4-(TBDMS-oxy)-1-Boc-L-proline
  • SMILES O=C(N1[C@H](C(O)=O)C[C@H](C1)O[Si](C)(C(C)(C)C)C)OC(C)(C)C

Description

This pyrrolidine derivative features a tert-butoxycarbonyl-protected amine and a silyl ether-stabilized hydroxyl group, enabling orthogonal handling in complex peptide synthesis. The stereochemistry at C2 and C4 ensures high diastereoselectivity during coupling steps.

Application

(2S,4R)-1-(tert-Butoxycarbonyl)-4-((tert-butyldimethylsilyl)oxy)pyrrolidine-2-carboxylic acid serves as a versatile chiral building block for the synthesis of pyrrolidine-containing bioactive molecules. The protected amine and silylated hydroxyl groups provide orthogonal functionality, enabling selective transformations in multi-step sequences. Bench-stable and compatible with standard coupling conditions, it facilitates efficient access to complex heterocyclic scaffolds used in medicinal chemistry and peptide analog development.

Synthesis

  • Route1

    References

    • Sato; Kawasaki; Oda; Yagi; El Bialy; Uenishi; Yamauchi; Ikeda Journal of the Chemical Society. Perkin Transactions 1, 2001 , # 20 p. 2623 - 2631
  • Route2

    References

    • Watts, John; Luu, Lien; McKee, Vickie; Carey, Ed; Kelleher, Fintan Advanced Synthesis and Catalysis, 2012 , vol. 354, # 6 p. 1035 - 1042
  • Route3

    References

    • Watts, John; Luu, Lien; McKee, Vickie; Carey, Ed; Kelleher, Fintan Advanced Synthesis and Catalysis, 2012 , vol. 354, # 6 p. 1035 - 1042

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H315-H319
Precautionary Statements : P264-P280-P302+P352-P362+P364

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Computational Chemistry Data

  • TPSA   76.07
  • LogP   3.4708
  • H_Acceptors   4
  • H_Donors   1
  • Rotatable_Bonds   3

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