CAS 109838-85-9: (R)-2,5-dihydro-3,6-dimethoxy-2-iso-propylpyrazine

Stability Moisture Sensitive Applications An inhibitor with antitumor activity. References Plumb, J., et al.: Mol. Cancer Ther., 2, 721 (2003), de Ruijter, A., et al.: Biochem. J., 370, 737 (2003), Dey, P., et al.: Curr. Med. Chem., 13, 2909 (2006), Maiso, P., et al.: Cancer Res., 66, 5781 (2006), Paris, M., et al.: J. Med. Chem., 51, 1505 (2008),

(R)-3-Isopropyl-2,5-dimethoxy-3,6-dihydropyrazine

(R)-3-Isopropyl-2,5-dimethoxy-3,6-dihydropyrazineChiral auxiliary for the synthesis of α-amino acids. It is an inhibitor with antitumor activity. This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.

(R)-2,5-Dihydro-3,6-dimethoxy-2-isopropylpyrazine and its enantiomer (S)-2,5-Dihydro-3,6-dimethoxy-2-isopropylpyrazine are also known as Schöllkopf chiral auxiliaries or Schöllkopf reagents, and are used to produce optically pure α-amino acids via asymmetric synthesis. The Schöllkopf reagent can be deprotonated at the prochiral α-carbon, and the resulting enolate is trapped with electrophiles to yield adducts with high (typically > 95% d.e.) diastereoselectivity. The enolate is essentially planar, and the steric bulk of the isopropyl group directs the incoming electrophile to attack from the opposite face, yielding trans adducts. A wide range of electrophiles including alkyl halides, alkyl sulfonates, acyl chlorides, aldehydes, ketones, epoxides, thioketones and enones can be used. Hydrolysis, typically under mild acidic conditions, yields the non-substituted amino acid with high (typically > 95 e.e.) enantiopurity.