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(3R,6R)-3,6-Dimethyl-1,4-dioxane-2,5-dione

  • CAS No. 13076-17-0

  • Cat. No. CS-0158241
  • Molecule weightNone
  • Purity≥98%
  • MDL No.MFCD00082566

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

(3R,6R)-3,6-Dimethyl-1,4-dioxane-2,5-dione|CS-0158241

Structure of 13076-17-0

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General Information

  • CAS No. 13076-17-0
  • Cat. No. CS-0158241
  • Purity ≥98%
  • MDL No. MFCD00082566
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₈O₄
  • Molecular Weight None
  • Synonym(s) (3R,6R)-3,6-Dimethyl-1,4-dioxane-2,5-dione
  • SMILES O=C([C@@H](C)O1)O[C@H](C)C1=O

Description

This chiral dioxane derivative features a rigid, electron-deficient 1,4-dioxane core with defined stereochemistry at the 3 and 6 positions. It serves as a stable, bench-ready synthon for asymmetric synthesis, integrating readily into cyclic systems via Diels-Alder or nucleophilic addition pathways.

Application

(3R,6R)-3,6-Dimethyl-1,4-dioxane-2,5-dione serves as a stable, bench-ready diacid precursor enabling efficient construction of chiral heterocyclic scaffolds. Its defined stereochemistry facilitates controlled ring-opening reactions and functional group transformations, supporting applications in asymmetric synthesis and the preparation of biologically relevant motifs. The compound exhibits excellent stability, simplifies purification, and demonstrates broad compatibility with standard coupling and reduction protocols.

Synthesis

  • Route1
    • null|null
      849585-22-4
    • ~%
    • In-stock
      (3R,6R)-3,6-Dimethyl-1,4-dioxane-2,5-dione|CS-0158241
      13076-17-0

    References

    • Futerro S.A.; Coszach, Philippe; Mariage, Pierre-Antoine Patent: US8592609 B2, 2013 ; Location in patent: Page/Page column 3; 4; 5 ;
  • Route2
    • null|null
      1071822-17-7
    • ~%
    • (3R,6S)-3,6-Dimethyl-1,4-dioxane-2,5-dione|CS-0634577
      13076-19-2
    • In-stock
      (3R,6R)-3,6-Dimethyl-1,4-dioxane-2,5-dione|CS-0158241
      13076-17-0

    References

    • Jing, Feng; Hillmyer, Marc A. Journal of the American Chemical Society, 2008 , vol. 130, # 42 p. 13826 - 13827
  • Route3
    • null|null
      849585-22-4
    • ~%
    • (3R,6S)-3,6-Dimethyl-1,4-dioxane-2,5-dione|CS-0634577
      13076-19-2
    • In-stock
      (3R,6R)-3,6-Dimethyl-1,4-dioxane-2,5-dione|CS-0158241
      13076-17-0

    References

    • Futerro S.A.; Coszach, Philippe; Mariage, Pierre-Antoine Patent: US8592609 B2, 2013 ; Location in patent: Page/Page column 3; 4; 5 ;

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H319
Precautionary Statements : P264-P280-P305+P351+P338-P337+P313

Quality Control

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Computational Chemistry Data

  • TPSA   52.6
  • LogP   -0.1366
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   0

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