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Benzyl (2S,4R)-4-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate

  • CAS No. 95687-41-5

  • Cat. No. CS-0021635
  • Purity≥96%
  • MDL No.MFCD03427085

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

Benzyl (2S,4R)-4-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate|CS-0021635

Structure of 95687-41-5

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General Information

  • CAS No. 95687-41-5
  • Cat. No. CS-0021635
  • Purity ≥96%
  • MDL No. MFCD03427085
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₃H₁₇NO₄
  • Molecular Weight None
  • Synonym(s) N-Cbz-trans-4-hydroxy-L-prolinol
  • SMILES O=C(N1[C@H](CO)C[C@@H](O)C1)OCC2=CC=CC=C2

Description

Benzyl (2S,4R)-4-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate features a stereodefined pyrrolidine core with orthogonal hydroxyl and hydroxymethyl groups, enabling selective functionalization in complex molecule synthesis. This bench-stable derivative integrates readily into peptide-like scaffolds and serves as a key chiral building block for bioactive compound development.

Application

Benzyl (2S,4R)-4-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate serves as a versatile chiral building block for the synthesis of bioactive heterocycles and pharmaceutical intermediates. Its defined stereochemistry enables reliable access to pyrrolidine-containing scaffolds, while the hydroxyl and carboxylate functionalities support orthogonal protection strategies. The benzyl ester group facilitates easy deprotection under standard conditions, enhancing utility in multi-step syntheses.

Synthesis

  • Route1

    References

    • DAIICHI PHARMACEUTICAL CO., LTD. Patent: EP1623975 A1, 2006 ; Location in patent: Page/Page column 20-21 ;
  • Route2

    References

    • Spirogen Limited Patent: EP1193270 A2, 2002 ; Location in patent: Page 14, 36, 105 ;
  • Route3
    • (2S)-1-((Benzyloxy)carbonyl)-4-hydroxypyrrolidine-2-carboxylic acid|CS-1701483
      197079-48-4
    • ~90%
    • In-stock
      Benzyl (2S,4R)-4-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate|CS-0021635
      95687-41-5

    References

    • Braish; Tamim F.; Fox; Darrell E. Patent: US5036153 A1, 1991 ;

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   70
  • LogP   0.7507
  • H_Acceptors   4
  • H_Donors   2
  • Rotatable_Bonds   3

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