Date published: 2026-4-24

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(DHQ)2Pyr (CAS 149820-65-5)

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Alternate Names:
Hydroquinine 2,5-diphenyl-4,6-pyrimidinediyl diether
Application:
(DHQ)2Pyr is a bis-Cinchona alkaloid ligand used in enantioselective synthesis applications
CAS Number:
149820-65-5
Purity:
≥97%
Molecular Weight:
881.11
Molecular Formula:
C56H60N6O4
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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(DHQ)2Pyr, or dihydroquinidine pyrrolidine, is a chiral bis-Cinchona alkaloid ligand used in enantioselective synthesis applications. This ligand is a structural analog of quinidine, a naturally occurring compound, and incorporates pyrrolidine to form a complex structure capable of inducing chirality in chemical reactions. (DHQ)2Pyr is particularly valued for its effectiveness in catalyzing asymmetric reactions, which include but are not limited to, asymmetric epoxidation, Diels-Alder reactions, and Michael additions. These reactions are foundational in building complex, chiral molecules from simpler substrates. The use of (DHQ)2Pyr in asymmetric synthesis not only allows for the production of chiral molecules with high enantiomeric excess (a measure of purity in terms of chirality) but also exemplifies the importance of catalysis in modern organic synthesis.


(DHQ)2Pyr (CAS 149820-65-5) References

  1. Enantioselective amination of alpha-phenyl-alpha-cyanoacetate catalyzed by chiral amines incorporating the alpha-phenylethyl auxiliary.  |  Liu, Y., et al. 2007. J Org Chem. 72: 1522-5. PMID: 17288398
  2. Anti-AIDS agents 79. Design, synthesis, molecular modeling and structure-activity relationships of novel dicamphanoyl-2',2'-dimethyldihydropyranochromone (DCP) analogs as potent anti-HIV agents.  |  Zhou, T., et al. 2010. Bioorg Med Chem. 18: 6678-89. PMID: 20728367
  3. Studies toward the unique pederin family member psymberin: full structure elucidation, two alternative total syntheses, and analogs.  |  Feng, Y., et al. 2012. J Am Chem Soc. 134: 17083-93. PMID: 23004238
  4. Catalytic, asymmetric halofunctionalization of alkenes--a critical perspective.  |  Denmark, SE., et al. 2012. Angew Chem Int Ed Engl. 51: 10938-53. PMID: 23011853
  5. E2 enzyme inhibition by stabilization of a low-affinity interface with ubiquitin.  |  Huang, H., et al. 2014. Nat Chem Biol. 10: 156-163. PMID: 24316736
  6. Synthetic studies of alkaloids containing pyrrolidine and piperidine structural motifs.  |  Bhat, C. 2015. ChemistryOpen. 4: 192-6. PMID: 25969818
  7. 1H-Imidazol-4(5H)-ones and thiazol-4(5H)-ones as emerging pronucleophiles in asymmetric catalysis.  |  Mielgo, A. and Palomo, C. 2016. Beilstein J Org Chem. 12: 918-36. PMID: 27340482
  8. Modern Approaches for Asymmetric Construction of Carbon-Fluorine Quaternary Stereogenic Centers: Synthetic Challenges and Pharmaceutical Needs.  |  Zhu, Y., et al. 2018. Chem Rev. 118: 3887-3964. PMID: 29608052
  9. A Chlorine-Atom-Controlled Terminal-Epoxide-Initiated Bicyclization Cascade Enables a Synthesis of the Potent Cytotoxins Haterumaimides J and K.  |  Michalak, SE., et al. 2019. J Am Chem Soc. 141: 9202-9206. PMID: 31129963
  10. Evaluation of an octahydroisochromene scaffold used as a novel SARS 3CL protease inhibitor.  |  Yoshizawa, SI., et al. 2020. Bioorg Med Chem. 28: 115273. PMID: 31926775
  11. The Formosalides: Structure Determination by Total Synthesis.  |  Schulthoff, S., et al. 2021. Angew Chem Int Ed Engl. 60: 446-454. PMID: 32946141
  12. Synthetic and computational efforts towards the development of peptidomimetics and small-molecule SARS-CoV 3CLpro inhibitors.  |  Paul, A., et al. 2021. Bioorg Med Chem. 46: 116301. PMID: 34332853
  13. Synthetic efforts on the road to marine natural products bearing 4-O-2,3,4,6-tetrasubstituted THPs: an update.  |  Fariña-Ramos, M., et al. 2021. RSC Adv. 11: 5832-5858. PMID: 35423108
  14. The Synthesis and Glycoside Formation of Polyfluorinated Carbohydrates.  |  Huonnic, K. and Linclau, B. 2022. Chem Rev. 122: 15503-15602. PMID: 35613331

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

(DHQ)2Pyr, 1 g

sc-227755
1 g
$297.00