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    • 1. 发明授权
    • Optically active 2,2-dimethyl-1,3-dioxin-4-ones and method for preparing
same and method for preparing optically active compound for synthesis
of physiologically active substance and optically active intermediate
compound
    • 光学活性的2,2-二甲基-1,3-二恶英-4-酮及其制备方法以及制备用于合成生理活性物质和光学活性中间体化合物的光学活性化合物的方法
    • US5292891A
    • 1994-03-08
    • US991551
    • 1992-12-15
    • Chikara KanekoMasayuki Sato
    • Chikara KanekoMasayuki Sato
    • C07D301/27C07D303/42C07D309/30C07D309/36C07D319/06C12P17/06C12P41/00C07D309/10
    • C07D319/06C07D303/42C07D309/30C07D309/36C12P17/06C12P41/004
    • There are provided novel and optically active 2,2-dimethyl-1,3-dioxin-4-ones which are useful as starting materials for physiologically active compounds, functional materials or the like. Provided are optically active 5,6-epoxyhexanoic acid esters and novel optically active 6-substituted tetrahydropyran-2-one derivatives. That is, optically active 6-chloromethyltetrahydropyran-2-one can be synthesized by lactonizing optically active 2,2-dimethyl-6-(3-chloro-2-hydroxypropyl)-1,3-dioxin-4-one to form optically active 6-chloromethyltetrahydropyran-2,4-dione; reacting the thus formed compound with hydrogen in the presence of a catalyst to obtain optically active 6-chloromethyl-4-hydroxytetrahydropyran-2-one; subjecting this compound to a dehydration reaction, thereby obtaining optically active 6-chloromethyldihydropyran-2-one; reacting this compound with hydrogen in the presence of a catalyst to form optically active 6-chloromethyltetrahydropyran-2-one; and then treating this compound under basic conditions to prepare an optically active 5,6-epoxyhexanoic acid ester represented by the formula (6) ##STR1## (wherein the symbol * represents an asymmetric carbon atom, and R is a methyl group or an ethyl group).
    • 提供了可用作生理活性化合物,功能材料等的起始原料的新型和光学活性的2,2-二甲基-1,3-二恶英-4-酮。 提供光学活性的5,6-环氧己酸酯和新的光学活性的6-取代的四氢吡喃-2-酮衍生物。 也就是说,光学活性的6-氯甲基四氢吡喃-2-酮可以通过将光学活性的2,2-二甲基-6-(3-氯-2-羟丙基)-1,3-二恶英-4-酮内酯化来形成光学活性的 6-氯甲基四氢吡喃-2,4-二酮; 使这样形成的化合物与氢气在催化剂存在下反应,得到光学活性的6-氯甲基-4-羟基四氢吡喃-2-酮; 使该化合物脱水反应,得到光学活性的6-氯甲基二氢吡喃-2-酮; 在催化剂存在下使该化合物与氢气反应形成光学活性的6-氯甲基四氢吡喃-2-酮; 然后在碱性条件下处理该化合物以制备由式(6)表示的光学活性5,6-环氧己酸酯(*化学结构*)(6)(其中符号*表示不对称碳原子,R为 甲基或乙基)。