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CS-W001157 4
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(R)-4-Benzyl-3-(3-methylbutanoyl)oxazolidin-2-one

  • CAS No. 145589-03-3

  • Cat. No. CS-0154253
  • Purity≥98%
  • MDL No.MFCD10566718

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

(R)-4-Benzyl-3-(3-methylbutanoyl)oxazolidin-2-one|CS-0154253

Structure of 145589-03-3

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General Information

  • CAS No. 145589-03-3
  • Cat. No. CS-0154253
  • Purity ≥98%
  • MDL No. MFCD10566718
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₅H₁₉NO₃
  • Molecular Weight 261.32
  • Synonym(s) 2-Oxazolidinone, 3-(3-methyl-1-oxobutyl)-4-(phenylmethyl)-, (R)-
  • SMILES CC(C)CC(=O)N1[C@H](CC2=CC=CC=C2)COC1=O

Description

(R)-4-Benzyl-3-(3-methylbutanoyl)oxazolidin-2-one is a chiral oxazolidinone scaffold featuring a benzylic stereocenter and a sterically hindered acyl group. This configuration enhances diastereoselectivity in asymmetric synthesis, particularly in nucleophilic additions and enantioselective transformations. The molecule exhibits bench-stable handling characteristics and compatibility with common organic solvents, enabling straightforward integration into synthetic sequences requiring stereocontrol.

Application

(R)-4-Benzyl-3-(3-methylbutanoyl)oxazolidin-2-one serves as a robust chiral auxiliary in asymmetric synthesis, enabling stereoselective C–C bond formation through well-established enolate chemistry. Its oxazolidinone core provides excellent diastereoselectivity in aldol and alkylation reactions, with bench-stable handling and straightforward purification. The benzyl and isovaleryl substituents offer orthogonal reactivity and compatibility across standard synthetic workflows.

Synthesis

  • Route1
    • (S)-4-Benzyl-2-oxazolidinone Brivaracetam  Impurity|CS-0228893
      90719-32-7
    • null|null
      108-12-3
    • ~99%
    • In-stock
      (R)-4-Benzyl-3-(3-methylbutanoyl)oxazolidin-2-one|CS-0154253
      145589-03-3

    References

    • Nam, Gyeok; Ko, Soo Y. Helvetica Chimica Acta, 2012 , vol. 95, # 10 p. 1937 - 1945,9
  • Route2
    • In-stock
      Isovaleric acid (mixture of isomers),98%(isomers mixture)|CS-0881782
      503-74-2
    • (S)-4-Benzyl-2-oxazolidinone Brivaracetam  Impurity|CS-0228893
      90719-32-7
    • ~92%
    • In-stock
      (R)-4-Benzyl-3-(3-methylbutanoyl)oxazolidin-2-one|CS-0154253
      145589-03-3

    References

    • Jiao, Zhi-Gang; Chang, Xiao-Wei; Ding, Wei; Liu, Guo-Jun; Song, Ke-Sheng; Zhu, Nian-Yong; Zhang, Dan-Wei; Yang, Dan Chemistry - An Asian Journal, 2011 , vol. 6, # 7 p. 1791 - 1799
  • Route3
    • In-stock
      Locostatin|CS-0136354
      90719-30-5
    • null|null
      1184-58-3
    • ~58%
    • In-stock
      (R)-4-Benzyl-3-(3-methylbutanoyl)oxazolidin-2-one|CS-0154253
      145589-03-3

    References

    • Rueck, Karola; Kunz, Horst Synthesis, 1993 , # 10 p. 1018 - 1028

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   46.61
  • LogP   2.6226
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   4

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