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    • 1. 发明专利
    • DE60315391D1
    • 2007-09-20
    • DE60315391
    • 2003-09-24
    • TOSOH CORP
    • KAGAWA TAKUMIKAMBARA TAKESHISAKKA HIDEOYANASE MANABU
    • C07D303/32C07B53/00C07C45/63C07C45/65C07C45/72C07C49/16C07C49/163C07C49/167C07C49/794C07C49/798C07C49/80C07C49/813C07C49/82C07C49/83C07D303/48
    • An optically active substituted (2S,3R)-epoxyenone derivative (I), is new. Optically active substituted (2S,3R)-epoxyenone derivative of formula (I) is new. [Image] R 1>methyl, ethyl or 3-10C alkyl; and R 2>optionally substituted phenyl or tert-butyl. Independent claims are also included for: (a) method (M) for preparation of (I) involving: asymmetrically oxidizing an enone of formula R 1>-CH=CH-C(=O)-R 2>(II); (b) an optically active (2R,3S)-epoxyester of formula (III); (c) method (M1) for preparation of (III) involving: oxidizing (I) with an oxidizing agent; (d) method (M2) for preparation of an optically active (2S,3R)-2,3-epoxypropionic acid of formula (IV) having a substituent at 3-position involving hydrolyzing (III); (e) 3-halogenopropan-1-one derivative of formula R 1>-CH(X)-CH 2-C(=O)-R 2>(V); (f) method (M3) for preparation of (V) involving reacting a beta -hydroxyketone derivative of formula R 1>-CH(OH)CH 2-C(=O)-R 2>(VI) with a hydrogen halide or hydrogen halide acid; (g) method (M4) for preparation of (II) involving treating (V) with a base; (h) method (M5) for preparation of an optically active 2,3-epoxy-3-cyclohexylpropionic acid or its ester involving: reacting an enzyme having an ability to asymmetrically hydrolyze an ester bond, to a mixture of (2R,3S)-2,3-epoxy-3-cyclohexylpropionate and a (2R,3S)-2,3-epoxy-3-cyclohexylpropionate, of the 2,3-epoxy-3-cyclohexylpropionate of formula (VII) for stereoselective hydrolysis, followed by separation and purification. [Image] X : halo; A : optionally substituted cyclohexyl; and R 3>ester.
    • 6. 发明专利
    • DE60315391T2
    • 2008-04-17
    • DE60315391
    • 2003-09-24
    • TOSOH CORP
    • KAGAWA TAKUMIKAMBARA TAKESHISAKKA HIDEOYANASE MANABU
    • C07D303/32C07B53/00C07C45/63C07C45/65C07C45/72C07C49/16C07C49/163C07C49/167C07C49/794C07C49/798C07C49/80C07C49/813C07C49/82C07C49/83C07D303/48
    • An optically active substituted (2S,3R)-epoxyenone derivative (I), is new. Optically active substituted (2S,3R)-epoxyenone derivative of formula (I) is new. [Image] R 1>methyl, ethyl or 3-10C alkyl; and R 2>optionally substituted phenyl or tert-butyl. Independent claims are also included for: (a) method (M) for preparation of (I) involving: asymmetrically oxidizing an enone of formula R 1>-CH=CH-C(=O)-R 2>(II); (b) an optically active (2R,3S)-epoxyester of formula (III); (c) method (M1) for preparation of (III) involving: oxidizing (I) with an oxidizing agent; (d) method (M2) for preparation of an optically active (2S,3R)-2,3-epoxypropionic acid of formula (IV) having a substituent at 3-position involving hydrolyzing (III); (e) 3-halogenopropan-1-one derivative of formula R 1>-CH(X)-CH 2-C(=O)-R 2>(V); (f) method (M3) for preparation of (V) involving reacting a beta -hydroxyketone derivative of formula R 1>-CH(OH)CH 2-C(=O)-R 2>(VI) with a hydrogen halide or hydrogen halide acid; (g) method (M4) for preparation of (II) involving treating (V) with a base; (h) method (M5) for preparation of an optically active 2,3-epoxy-3-cyclohexylpropionic acid or its ester involving: reacting an enzyme having an ability to asymmetrically hydrolyze an ester bond, to a mixture of (2R,3S)-2,3-epoxy-3-cyclohexylpropionate and a (2R,3S)-2,3-epoxy-3-cyclohexylpropionate, of the 2,3-epoxy-3-cyclohexylpropionate of formula (VII) for stereoselective hydrolysis, followed by separation and purification. [Image] X : halo; A : optionally substituted cyclohexyl; and R 3>ester.