(S)-2,5-Dihydro-3,6-dimethoxy-2-isopropylpyrazine

CAS: 78342-42-4

Ref. 3D-FD03725

Product Information

• Name: (S)-2,5-Dihydro-3,6-dimethoxy-2-isopropylpyrazine
• Synonyms: (S)-Schollkopf reagent(S)-2,5-Dimethoxy-3-isopropyl-3,6-dihydropyrazine, (S)-2-Isopropyl-3,6-dimethoxy-2,5-dihydropyrazine, (2S)-(+)-2,5-Dihydro-3,6-Dimethoxy-2-Isopropylpyrazine, (2S)-3,6-dimethoxy-2-(propan-2-yl)-2,5-dihydropyrazine
• CAS: 78342-42-4

Description

(S)-2,5-Dihydro-3,6-dimethoxy-2-isopropylpyrazine and its enantiomer, (R)-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.

• Brand: Biosynth

Chemical properties

• Molecular weight: 184.24 g/mol
• Formula: C₉H₁₆N₂O₂
• Purity: Min. 97%
• Color/Form: Colorless Clear Liquid
• InChI: InChI=1S/C9H16N2O2/c1-6(2)8-9(13-4)10-5-7(11-8)12-3/h6,8H,5H2,1-4H3
• InChI key: InChIKey=FCFWEOGTZZPCTO-UHFFFAOYSA-N
• SMILES: COC1=NC(C(C)C)C(OC)=NC1