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AssigneeChisso Corporation
InventorsChikara Kaneko, Masayuki Sato
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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).
A method for preparing an optically active compound for the synthesis of a physiologically active substance which comprises lactonizing optically active 2,2-dimethyl-6-(3-chloro-2-hydroxypropyl)-1,3-dioxin-4-one represented by formula (1) ##STR31## to form optically active 6-chloromethyltetrahydropyran-2,4-dione represented by formula (2) ##STR32## reacting the thus formed compound with hydrogen in the presence of a catalyst to obtain optically active 6-chloromethyl-4-hydroxytetrahydropyran-2-one represented by formula (3), ##STR33## subjecting the compound of formula (3) to a dehydration reaction, thereby obtaining optically active 6-chloromethyldihydropyran-2-one represented by formula (4), ##STR34## reacting the compound of formula (4) with hydrogen in the presence of a catalyst to form optically active 6-chloromethyltetrahydropyran-2-one represented by the formula (5), ##STR35## and treating the compound of the formula (5) in an alcohol solvent under basic conditions to prepare an optically active 5,6-epoxyhexanoic acid ester represented by formula (6) ##STR36## (in each formula, the symbol * represents an asymmetric carbon atom, and R is a methyl group or an ethyl group).
A method for preparing an optically active compound for the synthesis of a physiologically active substance which comprises lactonizing optically active 2,2-dimethyl-6-(3-chloro-2-hydroxypropyl)-1,3-dioxin-4-one represented by the formula (1) ##STR37## to form optically active 6-chloromethyltetrahydropyran-2,4-dione represented by the formula (2), ##STR38## reacting the compound of formula (2) with hydrogen in the presence of a catalyst to obtain optically active 6-chloromethyl-4-hydroxytetrahydropyran-2-one represented by formula (3) ), ##STR39## subjecting the compound of formula (3) to a dehydration reaction to obtain optically active 6-chloromethyldihydropyran-2-one represented by the formula (4), ##STR40## and reacting the compound of formula (4) with hydrogen in the presence of a catalyst to obtain optically active 6-chloromethyltetrahydropyran-2-one represented by formula (5) ##STR41## (in each formula, the symbol * represents an asymmetric carbon atom).
Optically active 6-chloromethyltetrahydropyran-2,4-dione represented by formula (2):
Optically active 6-chloromethyl-4-hydroxytetrahydropyran-2-one represented by formula (3):
Optically active 6-chloromethyldihydropyran-2-one represented by formula (4):
Optically active 6-chloromethyltetrahydropyran-2-one represented by formula (5):
Dependencies are inferred from the claim text.