85120-75-8

Upstream product

• 108-05-4 vinyl acetate 
• 69617-84-1 rac-rhododendrol 
• 5471-51-2 4-(4-hydroxyphenyl)-2-oxobutane 

Downstream Products

• 129752-69-8 (R)-(+)-4-(4'-hydroxyphenyl)-2-butyl acetate 
• 59092-94-3 (R)-rhododendrol 

Relevant academic research and scientific papers

Asymmetric synthesis of enantiomerically pure zingerols by lipase-catalyzed transesterification and efficient synthesis of their analogues

The achiral zingerone 1, readily available from ginger, can be easily transformed into chiral derivatives. Zingerol 2, a reduced product of zingerone 1 is expected to be an important new medicinal lead compound. We have achieved a concise synthesis of optically active zingerol (R)-2 and (S)-2 by the lipase-catalyzed stereoselective transesterification of racemic 2. Under the optimized conditions, a lipase from Alcaligenes sp. (Meito QLM) and vinyl acetate in i-Pr2O or hexane at 35 C within 1 h gave the alcohol (S)-2 and the acetate (R)-9 with high enantioselectivity without producing acetylated by-products. Since optically active (S)-2 and (R)-9 were obtained through lipase-catalyzed transesterification, other enantiomerically pure novel compounds could all be synthesized.

Resolution of racemic rhododendrol by lipase-catalyzed enantioselective acetylation

Both (R)- and (S)-enantiomers of rhododendrol were prepared in high enantiomeric exess by lipase from Pseudomonas cepacia (Amano PS)-catalyzed acetylation of racemic 1 with vinyl acetate at room temperature. Especially, in the case of using acetonitrile as the solvent, by-products 4 and 5 were minimized.