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1. 发明授权

US5430171A T-butyl (R)-(-)-4-cyano-3-hydroxybutyrate and process for preparing the same 失效
标题翻译：（R） - （ - ） - 4-氰基-3-羟基丁酸叔丁酯及其制备方法
公开(公告)号：US5430171A
公开(公告)日：1995-07-04
申请号：US272623
申请日：1994-07-11
申请人： Shigeru Mitsuhashi , Kazutoshi Sakurai , Hidenori Kumobayashi
发明人： Shigeru Mitsuhashi , Kazutoshi Sakurai , Hidenori Kumobayashi
IPC分类号： C07C253/14 , C07C255/20 , C07C255/23 , C07C255/12
CPC分类号： C07C255/23
摘要： T-butyl (R)-(-)-4-cyano-3-hydroxybutyrate having an optical purity of 99%ee or higher and a process for producing the same are disclosed, the process comprising cyanogenation of a t-butyl (S)-(-)-4-halogeno-3-hydroxybutyrate obtained by enantioselective hydrogenation of a t-butyl 4-halogenoacetoacetate. Recrystallization of the resulting crude product gives the optically active compound with high optical purity.
摘要翻译：公开了光学纯度为99％ee以上的（R） - （ - ） - 4-氰基-3-羟基丁酸叔丁酯及其制备方法，该方法包括将（S） - （ - ） - 4-卤代-3-羟基丁酸酯，通过4-卤代乙酰乙酸叔丁酯的对映选择性氢化得到。所得粗产物的重结晶得到具有高光学纯度的光学活性化合物。

2. 发明授权

US5286883A (3R,5S)-3,5,6-trihydroxyhexanoic acid derivative and production method thereof 失效
标题翻译：（3R，5S）-3,5,6-三羟基己酸衍生物及其制备方法
公开(公告)号：US5286883A
公开(公告)日：1994-02-15
申请号：US976498
申请日：1992-11-13
申请人： Kazutoshi Sakurai , Shigeru Mitsuhashi , Hidenori Kumobayashi
发明人： Kazutoshi Sakurai , Shigeru Mitsuhashi , Hidenori Kumobayashi
IPC分类号： B01J31/24 , C07B53/00 , C07B61/00 , C07D309/12 , C07D319/06
CPC分类号： C07D319/06 , C07D309/12
摘要： A (3R,5S)-3,5,6-trihydroxyhexanoic acid derivative and a process of producing the (3R,5S)-3,5,6-trihydroxyhexanoic acid derivative which comprises the step of enantioselectively hydrogenating an (S)-5,6-dihydroxy-3-oxohexanoic acid derivative with a specific ruthenium-optically active phosphine complex represented as a catalyst are disclosed. The (3R,5S)-3,5,6-trihydroxyhexanoic acid derivative which is a useful compound capable of being easily converted into a lactone moiety, which is the active part of an inhibitor on HMG-CoA reductase, can be easily and efficiently obtained under a mild reaction condition with a high selectivity for the syn-diol form.
摘要翻译： A（3R，5S）-3,5,6-三羟基己酸衍生物和（3R，5S）-3,5,6-三羟基己酸衍生物的制备方法，其包括以下步骤：对（S）-5 公开了以表示为催化剂的特定钌光学活性膦配合物的6-二羟基-3-氧代己酸衍生物。作为HMG-CoA还原酶抑制剂的活性成分的能够容易地转化为内酯部分的有用化合物的（3R，5S）-3,5,6-三羟基己酸衍生物可以容易且有效地在温和的反应条件下以对顺式二醇形式的高选择性获得。

3. 发明授权

US5349107A Process for producing optically active .gamma.-hydroxyketones 失效
标题翻译：光学活性γ-羟基酮的制备方法
公开(公告)号：US5349107A
公开(公告)日：1994-09-20
申请号：US130173
申请日：1993-10-01
申请人： Seiji Watanabe , Shigeru Mitsuhashi , Hidenori Kumobayashi
发明人： Seiji Watanabe , Shigeru Mitsuhashi , Hidenori Kumobayashi
IPC分类号： C07C45/64 , C07C49/17 , C07C49/245 , C07C49/82
CPC分类号： C07C49/82 , C07C45/64 , C07C49/17 , C07C49/245
摘要： Disclosed herein is a process for producing a .gamma.-hydroxyketone (2), which comprises asymmetrically hydrogenating a .gamma.-diketone (1) in the presence of a ruthenium-optically active phosphine complex as a catalyst ##STR1## wherein R.sup.1 and R.sup.2 mean individually an alkyl or phenyl group which may have a substituent group. According to the invention, optically active .gamma.-hydroxyketones useful in synthesizing optically active moiety in, biodegradable polymers, perfumes, intermediates for synthesizing medicines and the like can be efficiently prepared.
摘要翻译：本文公开了一种制备γ-羟基酮（2）的方法，其包括在作为催化剂的钌光学活性膦配合物存在下不对称氢化γ-二酮（1），其中R 1和R 2分别表示可以具有取代基的烷基或苯基。根据本发明，可以有效地制备可用于合成光学活性部分的光学活性γ-羟基酮，可生物降解的聚合物，香料，用于合成药物的中间体等。

4. 发明授权

US4520212A Process for producing myrcenol 失效
标题翻译：制备月桂烯醇的方法
公开(公告)号：US4520212A
公开(公告)日：1985-05-28
申请号：US563810
申请日：1983-12-21
申请人： Shigeru Mitsuhashi , Hidenori Kumobayashi , Susumu Akutagawa
发明人： Shigeru Mitsuhashi , Hidenori Kumobayashi , Susumu Akutagawa
IPC分类号： B01J31/00 , C07B61/00 , C07C27/00 , C07C29/00 , C07C33/02 , C07C67/00 , C07F15/00
CPC分类号： C07C33/02 , C07C29/00 , C07F15/006 , C07B2200/07
摘要： Myrcenol is produced in an effecient, high yield and economical process by deaminating 7-hydroxygeranyl dialkylamine or 7-hydroxyneryl dialkylamine with a specific palladium-phosphine-cation complex catalyst represented by the formula[
摘要翻译：通过用式[[：PdL] + X-表示的特定的钯 - 膦 - 阳离子配合物催化剂使7-羟基蒎烷基二烷基胺或7-羟基腈基二烷基胺脱氨，以有效的，高产率和经济的方法制备月桂烯醇。代表乙烯基，L代表叔膦，X代表抗衡阴离子。

5. 发明授权

US5837877A Process for preparing optically active 4-hydroxy-2-pyrrolidone 失效
标题翻译：制备光学活性4-羟基-2-吡咯烷酮的方法
公开(公告)号：US5837877A
公开(公告)日：1998-11-17
申请号：US790931
申请日：1997-01-29
申请人： Shigeru Mitsuhashi , Hidenori Kumobayashi
发明人： Shigeru Mitsuhashi , Hidenori Kumobayashi
IPC分类号： B01J31/24 , C07B53/00 , C07B61/00 , C07D207/26 , C07D207/273
CPC分类号： C07D207/273
摘要： A process for preparing optically active 4-hydroxy-2-pyrrolidone comprising asymmetrically hydrogenating an N-substituted-4-amino-3-oxobutanoic ester represented by formula (I): ##STR1## wherein R.sup.1 represents a benzyloxycarbonyl group, the benzene ring of which may be substituted; and R.sup.2 represents a lower alkyl group having 1 to 4 carbon atoms, in the presence of a ruthenium-optically active phosphine complex as a catalyst to obtain an optically active N-substituted-4-amino-3-hydroxybutanoic ester, deblocking, and cyclizing the ester. A series of the reactions can be carried out in one pot. Optically active 4-hydroxy-2-pyrrolidone is obtained in high yield with high optical purity, and is useful in the synthesis of carbapenem antibiotics
摘要翻译：一种制备光学活性的4-羟基-2-吡咯烷酮的方法，包括用式（I）表示的N-取代-4-氨基-3-氧代丁酸酯不对称氢化：其中R1代表苄氧基羰基，苯环可以被取代; 在钌光学活性膦配合物作为催化剂的存在下，R 2表示具有1〜4个碳原子的低级烷基，得到光学活性的N-取代-4-氨基-3-羟基丁酸酯，去封闭和环化酯。一系列反应可以在一锅中进行。以高光学纯度获得光学活性的4-羟基-2-吡咯烷酮，可用于合成碳青霉烯类抗生素

6. 发明授权

US06197996B1 Process for preparing optically active carnitine ester 失效
标题翻译：制备光学活性肉碱酯的方法
公开(公告)号：US06197996B1
公开(公告)日：2001-03-06
申请号：US08139861
申请日：1993-10-22
申请人： Takanao Taketomi , Toshiaki Sakaguchi , Hidenori Kumobayashi
发明人： Takanao Taketomi , Toshiaki Sakaguchi , Hidenori Kumobayashi
IPC分类号： C07C22900
CPC分类号： C07C227/32
摘要： A process for preparing an optically active carnitine ester represented by formula (I): wherein R represents a lower alkyl group; and X represents a halogen atom, is disclosed, comprises asymmetrically hydrogenating a &ggr;-trimethylammonium-3-oxobutanoic ester halide represented by formula (II): wherein R and X are as defined above, in the presence of a ruthenium-optically active phosphine complex as a catalyst. An optically active carnitine ester of any desired isomerism can be obtained through simple operation in high yield at high optical purity. The substrate used is easily available.
摘要翻译：一种制备由式（I）表示的光学活性肉碱酯的方法：其中R表示低级烷基; 并且X表示卤素原子，包括在钌光学活性膦配合物存在下不对称地氢化由式（II）表示的γ-三甲基铵-3-氧代丁酸酯卤化物：其中R和X如上所定义作为催化剂。可以通过在高光学纯度下以高产率的简单操作获得任何所需异构体的光学活性肉碱酯。使用的基材很容易获得。

7. 发明授权

US5756760A 1-substituted-2-diphenylphosphinonaphthalene and transition metal complex comprising the same as a ligand 失效
标题翻译： 1-取代-2-二苯基膦基萘和与配体相同的过渡金属络合物
公开(公告)号：US5756760A
公开(公告)日：1998-05-26
申请号：US812549
申请日：1997-03-07
申请人： Sotaro Miyano , Tetsutaro Hattori , Yasuko Komuro , Hidenori Kumobayashi
发明人： Sotaro Miyano , Tetsutaro Hattori , Yasuko Komuro , Hidenori Kumobayashi
IPC分类号： B01J31/24 , C07B53/00 , C07F9/572 , C07F15/00 , C07F9/02 , C07D207/00
CPC分类号： C07F9/5721 , C07F15/0046 , C07F15/006 , C07F15/008 , Y02P20/55
摘要： A 1-substituted-2-diphenylphosphinonaphthalene represented by formula (I): ##STR1## wherein at least one of R.sup.1, R.sup.2, R.sup.3, and R.sup.4, which may be the same or different, represents a lower alkyl group having 1 to 4 carbon atoms which may be substituted with an alkoxy group, a phenyl group or --OR.sup.6 (wherein R.sup.6 represents a hydrogen atom, a lower alkyl group having 1 to 4 carbon atoms or an alcohol-protective group), and the rest of them represent a hydrogen atom; A represents a single bond or a methylene group; and R.sup.5 represents a substituted or unsubstituted phenyl group; and a transition metal complex comprising the 1-substituted-2-diphenylphosphinonaphthalene as a ligand. The transition metal complex is useful as a catalyst in asymmetric synthesis.
摘要翻译：由式（I）表示的1-取代-2-二苯基膦基萘：其中R 1，R 2，R 3和R 4中至少有一个可以相同或不同，表示具有1 至4个可被烷氧基取代的碳原子，苯基或-OR 6（其中R6表示氢原子，碳原子数1〜4的低级烷基或醇保护基），其余的表示氢原子; A表示单键或亚甲基; R5表示取代或未取代的苯基; 以及包含1-取代-2-二苯基膦基萘作为配体的过渡金属络合物。过渡金属络合物可用作不对称合成中的催化剂。

8. 发明授权

US5631397A Process for producing optically active diaminohexanone derivative 失效
标题翻译：光学活性二氨基己酮衍生物的制备方法
公开(公告)号：US5631397A
公开(公告)日：1997-05-20
申请号：US470466
申请日：1995-06-06
申请人： Tetsuro Yamasaki , Hidenori Kumobayashi , Noboru Sayo , Toshiyuki Murayama , Noboru Sano , Takero Ishizaki
发明人： Tetsuro Yamasaki , Hidenori Kumobayashi , Noboru Sayo , Toshiyuki Murayama , Noboru Sano , Takero Ishizaki
IPC分类号： B01J31/22 , B01J31/24 , C07B61/00 , C07C215/28 , C07C221/00 , C07C225/16 , C07C231/12 , C07C231/18 , C07C233/36 , C07C233/43 , C07C233/78 , C07C269/06 , C07C271/20
CPC分类号： C07C221/00 , C07C231/12 , C07C231/18 , C07C233/36 , C07C233/78 , C07C269/06 , C07C271/20
摘要： Disclosed herein is a process for producing a (2S,5S)-2,5-diamino-1,6-diphenyl-3-hexanone derivative represented by the formula (1): ##STR1## wherein R.sup.1 means a lower alkylcarbonyl group, a halogen-substituted lower alkylcarbonyl group, an arylcarbonyl group or a lower alkoxycarbonyl group, and R.sup.2 and R.sup.3 are identical with or different from each other and denote individually an aryl group or an alkoxy-substituted aryl group, which comprises subjecting a (2S)-2,5-diamino-1,6-diphenyl-4-hexen-3-one derivative represented by the formula (2): ##STR2## wherein R.sup.1, R.sup.2 and R.sup.3 have the same meaning as defined above, to a hydrogenation reaction in the presence of a transition metal-containing catalyst.
摘要翻译：本文公开了一种制备由式（1）表示的（2S，5S）-2,5-二氨基-1,6-二苯基-3-己酮衍生物的方法：其中R1表示低级烷基羰基基团，卤素取代的低级烷基羰基，芳基羰基或低级烷氧基羰基，R 2和R 3彼此相同或不同，分别表示芳基或烷氧基取代的芳基，其包括使（ 2S）-2,5-二氨基-1,6-二苯基-4-己烯-3-酮衍生物：其中R1，R2和R3具有与上述相同的含义。在含过渡金属的催化剂存在下进行氢化反应。

9. 发明授权

US5606052A Substituted acetoxyazetidinone derivatives and process for preparing 4-acyloxyazetidinone derivatives 失效
标题翻译：取代的乙酰氧基氮杂环丁酮衍生物和制备4-酰氧基氮杂环丁酮衍生物的方法
公开(公告)号：US5606052A
公开(公告)日：1997-02-25
申请号：US436812
申请日：1995-05-08
申请人： Takao Saito , Hidenori Kumobayashi , Shunichi Murahashi
发明人： Takao Saito , Hidenori Kumobayashi , Shunichi Murahashi
IPC分类号： B01J27/128 , B01J31/12 , B01J31/30 , C07B61/00 , C07D205/08 , C07F7/18
CPC分类号： C07F7/186 , C07D205/08 , C07F7/1892
摘要： A process for preparing a 4-acyloxyazetidinone or a derivative thereof represented by formula (IV): ##STR1## wherein R.sup.1 represents a hydrogen atom, a lower alkyl group, a hydroxyethyl group, or a protected hydroxyethyl group; R.sup.3 represents an alkyl group having from 1 to 10 carbon atoms which may be substituted with a halogen atom, a cyano group, a lower alkoxy group or a phenyl group, or a substituted or unsubstituted phenyl group, provided that the .alpha.-positioned carbon atom of said alkyl group should not have more than two halogen atoms; and R.sup.4 represents a hydrogen atom, a lower alkyl group, or a lower alkoxycarbonyl group, which is useful as an intermediate for penem antibiotics is disclosed, comprising reacting azetidinone or a derivative thereof represented by formula (II): ##STR2## wherein R.sup.1 is as defined above, and R.sup.2 represents a hydrogen atom, a lower alkyl group, a lower alkoxycarbonyl group, or a carboxyl group, with a carboxylic acid represented by formula (III):R.sup.3 COOH (III)wherein R.sup.3 is as defined above, in the presence of (1) a transition metal compound selected from a ruthenium compound, an osmium compound, and a cobalt compound, (2) an aldehyde having 2 or more carbon atoms, provided that the carbon atom at the .alpha.-position thereof should not have two or more halogen atoms, and (3) oxygen. The compound (IV) can be prepared with safety through simple and easy operations.
摘要翻译：制备由式（Ⅳ）表示的4-酰氧基氮杂环丁酮或其衍生物的方法：原子，低级烷基，羟乙基或被保护的羟乙基; R3表示可以被卤素原子，氰基，低级烷氧基或苯基取代的具有1至10个碳原子的烷基或取代或未取代的苯基，条件是α-位置的碳原子的所述烷基不应具有多于两个的卤素原子; 其中R 4表示可用作Penem抗生素中间体的氢原子，低级烷基或低级烷氧基羰基，包括使由式（II）表示的氮杂环丁酮或其衍生物：其中R 1如上所定义，R 2表示氢原子，低级烷基，低级烷氧基羰基或羧基，与式（III）表示的羧酸：R3COOH（III）其中R3如上定义在（1）选自钌化合物，锇化合物和钴化合物的过渡金属化合物的存在下，（2）具有2个或更多个碳原子的醛，条件是其α位上的碳原子不应该有两个或更多的卤素原子，和（3）氧。化合物（IV）可以通过简单和容易的操作安全地制备。

10. 发明授权

US5599954A N-substituted-7-amino-5-hydroxy-3-oxoheptanoic acid derivatives and method for producing the same 失效
标题翻译： N-取代-7-氨基-5-羟基-3-氧代庚酸衍生物及其制备方法
公开(公告)号：US5599954A
公开(公告)日：1997-02-04
申请号：US592494
申请日：1996-01-26
申请人： Sigeru Mitsuhashi , Tsukasa Sotoguchi , Yoshifumi Yuasa , Hidenori Kumobayashi
发明人： Sigeru Mitsuhashi , Tsukasa Sotoguchi , Yoshifumi Yuasa , Hidenori Kumobayashi
IPC分类号： A61K31/21 , A61P3/06 , A61P43/00 , C07C231/12 , C07C233/83 , C07C269/06 , C07C271/16 , C07C271/22 , C07D309/12 , C07D315/00
CPC分类号： C07C233/83 , C07C271/22 , C07D309/12 , Y02P20/55
摘要： Compounds represented by the following general structural formula (1) and methods for producing the compounds: ##STR1## R.sup.1 represents a group such as benzyloxycarbonyl, R.sup.2 represents a lower alkyl group, R.sup.3 represents a hydrogen atom or a protecting group, each of M.sup.1 and M.sup.2 represents a metal atom, and n represents the atomic valence of M.sup.1. Intermediates for HMG-CoA reductase inhibitors can be prepared safely and easily from these compounds.
摘要翻译：由以下一般结构式（1）表示的化合物及其制备方法：R1表示苄氧羰基，R2表示低级烷基，R3表示氢原子或保护基，M1和M2各自表示金属原子，n表示M1的原子价。 HMG-CoA还原酶抑制剂的中间体可以从这些化合物中安全和容易地制备。

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