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rel-(3R,4S)-tert-Butyl 3,4-dihydroxypyrrolidine-1-carboxylate

  • CAS No. 186393-22-6

  • Cat. No. CS-B1567
  • Purity≥95%
  • MDL No.MFCD21919047

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

rel-(3R,4S)-tert-Butyl 3,4-dihydroxypyrrolidine-1-carboxylate|CS-B1567

Structure of 186393-22-6

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General Information

  • CAS No. 186393-22-6
  • Cat. No. CS-B1567
  • Purity ≥95%
  • MDL No. MFCD21919047
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₁₇NO₄
  • Molecular Weight None
  • Synonym(s) 1-Pyrrolidinecarboxylic acid, 3,4-dihydroxy-, 1,1-dimethylethyl ester, (3R,4S)-rel-
  • SMILES O=C(N1C[C@@H](O)[C@@H](O)C1)OC(C)(C)C

Description

rel-(3R,4S)-tert-Butyl 3,4-dihydroxypyrrolidine-1-carboxylate is a stereochemically defined pyrrolidine derivative featuring adjacent hydroxyl groups and a robust tert-butyl ester handle. This configuration enables direct incorporation into complex molecular architectures, particularly in the synthesis of bioactive heterocycles and natural product analogs. The molecule exhibits enhanced stability under standard bench conditions and facilitates efficient downstream transformations without racemization.

Application

rel-(3R,4S)-tert-Butyl 3,4-dihydroxypyrrolidine-1-carboxylate serves as a stereochemically defined diol building block for the synthesis of pyrrolidine-based scaffolds. Its bench-stable tert-butyl carbamate protection enables straightforward handling and purification, while the adjacent hydroxyl groups facilitate selective derivatization and orthogonal functionalization in complex molecule assembly. This compound functions effectively in standard coupling and cyclization protocols, supporting applications in medicinal chemistry and natural product synthesis.

Safety Information

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GHS Pictogram :
GHS No : GHS06
Signal Word : Danger
UN#: 2811
Class : 6.1
Packing Group : Ⅲ
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   -0.0411
  • H_Acceptors   4
  • H_Donors   2
  • Rotatable_Bonds   0

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