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CS-W001157 4
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N-Boc-dolaproine

  • CAS No. 120205-50-7

  • Cat. No. CS-B0750
  • Purity≥95%
  • MDL No.MFCD18157735

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

N-Boc-dolaproine|CS-B0750

Structure of 120205-50-7

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General Information

  • CAS No. 120205-50-7
  • Cat. No. CS-B0750
  • Purity ≥95%
  • MDL No. MFCD18157735
  • Storage 4°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₄H₂₅NO₅
  • Molecular Weight 287.36
  • Synonym(s) (2R,3R)-BOC-dolaproine
  • SMILES CO[C@H]([C@@H](C)C(O)=O)[C@H]1N(C(OC(C)(C)C)=O)CCC1

Description

N-Boc-dolaproine features a protected amine and a rigid, electron-deficient pyrrolidine core, enabling stable incorporation into complex peptide scaffolds. This bench-stable building block facilitates efficient access to bioactive alkaloid analogs through mild deprotection and downstream coupling reactions under standard conditions.

Application

N-Boc-dolaproine serves as a versatile building block for the synthesis of complex alkaloid scaffolds and bioactive heterocycles. Its Boc-protected amine enables orthogonal functional group manipulation, while the rigid indole core facilitates stereoselective transformations. The compound exhibits excellent bench stability and compatibility with standard coupling protocols, making it well-suited for iterative synthesis in medicinal chemistry campaigns.

Synthesis

  • Route1
    • (2R,3R)-3-((S)-1-(tert-Butoxycarbonyl)pyrrolidin-2-yl)-3-hydroxy-2-methylpropanoic acid|CS-0042410
      133565-38-5
    • null|null
      74-88-4
    • ~86%
    • In-stock
      N-Boc-dolaproine|CS-B0750
      120205-50-7

    References

    • Shioiri, Takayuki; Hayashi, Kyoko; Hamada, Yasumasa Tetrahedron, 1993 , vol. 49, # 9 p. 1913 - 1924
  • Route2
    • null|null
      159173-43-0
    • ~79%
    • In-stock
      N-Boc-dolaproine|CS-B0750
      120205-50-7

    References

    • Roux, Florence; Maugras, Isabelle; Poncet, Joel; Niel, Gilles; Jouin, Patrick Tetrahedron, 1994 , vol. 50, # 18 p. 5345 - 5360
  • Route3

    References

    • Tetrahedron Letters, , vol. 44, # 5 p. 937 - 940

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

Quality Control

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Computational Chemistry Data

  • TPSA   76.07
  • LogP   2.1216
  • H_Acceptors   4
  • H_Donors   1
  • Rotatable_Bonds   4

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