Method for Producing (Z)-2-Benzoyloxy-12-Heptadecene and (2S,12Z)-2-Hydroxy-12-Heptadecene and Method for Producing (2S,12Z)-2-Acetoxy-12-Heptadecene

摘要

Provided are methods including a method for industrially producing (2S,12Z)-2-acetoxy-12-heptadecene, which is, for example, a sex pheromone of pistachio twig borer. The methods can include a production method comprising a step of reacting racemic (2RS,12Z)-2-hydroxy-12-heptadecene with vinyl benzoate in the presence of a lipase to obtain a mixture of optically active (2R,12Z)-2-benzoyloxy-12-heptadecene of Formula (R,Z-2) and optically active (2S,12Z)-2-hydroxy-12-heptadecene of Formula (S,Z-1), a step of heating the mixture to distill out the optically active (2S,12Z)-2-hydroxy-12-heptadecene (S,Z-1), and a step of acetylating the optically active (2S,12Z)-2-hydroxy-12-heptadecene (S,Z-1) to obtain optically active (2S,12Z)-2-acetoxy-12-heptadecene of Formula (S,Z-3).;

主权项

1. A method for producing optically active (2R,12Z)-2-benzoyloxy-12-heptadecene, the method comprising the steps of:
reacting racemic (2RS,12Z)-2-hydroxy-12-heptadecene with vinyl benzoate in the presence of a lipase as an esterase to obtain a mixture of optically active (2R,12Z)-2-benzoyloxy-12-heptadecene represented by Formula (R,Z-2):and optically active (2S,12Z)-2-hydroxy-12-heptadecene represented by Formula (S,Z-1):and
heating the mixture for distilling off the optically active (2S,12Z)-2-hydroxy-12-heptadecene (S,Z-1) to obtain the optically active (2R,12Z)-2-benzoyloxy-12-heptadecene (R,Z-2) as a residue.