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    • 1. 发明申请
    • NEW PROCESS FOR MANUFACTURING OPTICALLY ACTIVE CARBOCYCLINE INTERMEDIATES
    • 制造光学活性炭中间体的新工艺
    • WO1988003526A1
    • 1988-05-19
    • PCT/DE1987000515
    • 1987-11-12
    • SCHERING AKTIENGESELLSCHAFTSKUBALLA, WernerDAHL, Helmut
    • SCHERING AKTIENGESELLSCHAFT
    • C07C177/00
    • C07D319/08C07C405/0083
    • Process for manufacturing cis-bicyclo[3.3.0]octane-2-aldehydes of formula (I), in which R1 and R2 jointly represent the double-bound residue -O-X-O-, with X as straight or branched-chain alkylene with 1-7 C-atoms or R1 and R2 accordingly represent the residue OR with R as a straight or branched-chain alkyl with 1-7 C atoms and R3 represents hydrogen, a saturated alkyl residue with 1-7 C atoms, an aralkyl residu with 7-10 C atoms, a tetrahydropyranyl residue, a trialkylsilyl residue with 1-6 C atoms in the alkyl whereby alkyl also can be substituted by phenyl, a dialkylphenylsilyl residue or alkyldiphenylsilyl residue with 1-16 C atoms in the alkyl, characterized by the fact that the diastereomeric amides of formula (II) are separated, whereby in said formula R1, R2 and R3 have the stated meanings, and in that the enantiomerically pure amide of formula (II) is reduced.
    • 制备式(I)的顺式 - 双环[3.3.0]辛烷-2-醛的方法,其中R 1和R 2共同代表双键残基-OXO-,X为直链或支链亚烷基, 7个C原子或R 1和R 2相应地表示残基OR,其中R为具有1-7个C原子的直链或支链烷基,R 3表示氢,具有1-7个C原子的饱和烷基残基,残基为7 -10 C原子,四氢吡喃基残基,烷基中含有1-6个C原子的三烷基甲硅烷基残基,其中烷基也可以被苯基,二烷基苯基甲硅烷基残基或烷基中具有1-16个碳原子的烷基二苯基甲硅烷基残基取代,其特征在于 分离式(II)的非对映体酰胺,其中在所述式R1中,R2和R3具有所述含义,并且由式(II)的对映体纯的酰胺还原。
    • 6. 发明申请
    • RACEMIC DISSOCIATION OF 3-ACYLOXILIC-BICYCLO[3.3.0]OCTANE-7-ONE-2-CARBOXYLIC ACID ESTERS BY STEREOSPECIFIC ENZYME OR MICROBIOLOG ICAL ACYLATE HYDROLYSIS
    • 3-ACYLOXILIC-BICYCLO [3.3.0]季铵化合物的7-二-2-羧酸酯的立体解离通过立体酶或微生物酸性水解
    • WO1988003567A1
    • 1988-05-19
    • PCT/DE1987000513
    • 1987-11-12
    • SCHERING AKTIENGESELLSCHAFTPETZOLDT, KarlDAHL, HelmutSKUBALLA, Werner
    • SCHERING AKTIENGESELLSCHAFT
    • C12P41/00
    • C07D317/72C07C405/0083C07D319/08C12P7/26C12P7/42C12P7/62C12P17/02C12P41/004
    • Process for the production of optically active (+)-bicyclo[3.3.0]octanol derivatives of formula (+)-I, in which R1 and R2 represent jointly an oxygen atom or the double-bond residue -O-X-O-, with X as a straight or branched-chain alkylene with 1-7 C-atoms, or R1 and R2 represent separately the residue OR5, with R5 as a straight or branched-chain alkyl with 1-7 C-atoms, and R3 the residue COOZ with Z as a hydrogen atom, straight or branched chain alkyl with 1-7 C atoms, cycloalkyl with 3-6 C atoms, phenyl or aralkyl with 7-10 C atoms or R3 is the residue -(CH2)n-O-COR4, with n having the meaning 1-4 and R4 as a straight or branched-chain alkyl with 1-7 C atoms, cycloalkyl with 3-6 C atoms, phenyl or aralkyl with 7-10 C atoms. The process is characterized in that racemic 3 alpha -cyloxy-cis-bicyclo[3.3.0]-octane derivatives of formula (+/-)-II, wherein R1, R2, R3 and R4 have the above meanings, are subjected enzymatically or microbiologically to a stereospecific acylate hydrolysis and the (+)-bicyclo[3.3.0]-octanol derivative produced is separated from the unsaponified bicyclo[3.3.0]-octanol acylate of formula (-)-II or the unsaponified enantiomers (+)-II are separated from the saponified bicyclo[3.3.0]octanol derivative (-)-I and then subjected to chemical acylate hydrolysis.
    • 制备式(+) - I的光学活性(+) - 双环[3.3.0]辛醇衍生物的方法,其中R 1和R 2共同表示氧原子或双键残基-OXO-,其中X为 具有1-7个C原子的直链或支链亚烷基,或R1和R2分别表示残基OR5,R5表示具有1-7个C原子的直链或支链烷基,R3表示残基COOZ与Z 作为氢原子,具有1-7个C原子的直链或支链烷基,具有3-6个C原子的环烷基,具有7-10个C原子的苯基或芳烷基或R3是残基 - (CH 2)n O-COR 4,其中n具有 含1-4个碳原子的直链或支链烷基,含3-6个碳原子的环烷基,含有7-10个C原子的苯基或芳烷基。 该方法的特征在于其中R1,R2,R3和R4具有上述含义的式(+/-) - II的外消旋3α-甲氧基 - 顺式 - 二环[3.3.0] - 辛烷衍生物经酶促或 将微生物学上的立体定向酰化物水解,并将所产生的(+) - 双环[3.3.0] - 辛醇衍生物与式( - ) - II的未皂化的双环[3.3.0] - 辛醇酰化物或未掺杂的对映异构体(+) -II与皂化的双环[3.3.0]辛醇衍生物( - ) - I分离,然后进行化学酰化物水解。