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1. 发明授权

US5322955A Method of manufacturing 3-DPA-lactone 失效
标题翻译：制备3-DPA-内酯的方法
公开(公告)号：US5322955A
公开(公告)日：1994-06-21
申请号：US938238
申请日：1992-10-22
申请人： Katsuya Matsumoto , Takashi Ebata , Hiroshi Kawakami , Koshi Koseki , Hajime Matsushita
发明人： Katsuya Matsumoto , Takashi Ebata , Hiroshi Kawakami , Koshi Koseki , Hajime Matsushita
IPC分类号： C07D307/33 , C07D233/00
CPC分类号： C07D307/33 , Y02P20/55
摘要： In the method of the present invention for manufacturing 3-DPA-lactone, a protective group is introduced in the first step into the hydroxyl group at 4-position of .gamma.-ribonolactone by an ordinary method. Then, an acid anhydride or an acid chloride is added in the presence of a tertiary amine compound so as to conduct a .beta.-elimination of the hydroxyl group at the 3-position. As a result, a double bond is formed between the 2- and 3-positions and, at the same time, the hydroxyl group at the 2-position is acylated. The double bond between the 2- and 3-positions is reduced in the next step by means of a catalytic hydrogenation. Finally, the protective group of the hydroxyl group is eliminated by an ordinary method. The particular method permits using readily available raw materials, decreasing the number of manufacturing steps, and easily and selectively synthesizing the desired 3-DPA-lactone, which is hardly obtained from nature in a large amount, in high yield, compared with the conventional method.
摘要翻译： PCT No.PCT / JP92 / 00186 Sec。 371日期：1992年10月22日 102（e）日期1992年10月22日PCT提交1992年2月21日PCT公布。第WO92 / 14721号公报日本9月3日。在本发明的制备3-DPA-内酯的方法中，通过常规方法，将第一步中的保护基引入γ-内酯的4-位的羟基。然后，在叔胺化合物的存在下加入酸酐或酰氯，以在3-位进行羟基的β-烯丙基化。结果，在2-位和3-位之间形成双键，并且同时将2-位的羟基酰化。通过催化氢化，在下一步骤中2-和3-位之间的双键被还原。最后，通过常规方法除去羟基的保护基。该特定方法与常规方法相比，允许使用容易获得的原料，减少制造步骤的数量，并且容易且有选择地合成从大量难以获得的大量难以获得的所需3-DPA-内酯。

2. 发明授权

US5451689A Method of preparing epoxide 失效
标题翻译：环氧化物的制备方法
公开(公告)号：US5451689A
公开(公告)日：1995-09-19
申请号：US170191
申请日：1993-12-30
申请人： Katsuya Matsumoto , Takashi Ebata , Koshi Koseki , Koji Okano , Hiroshi Kawakami , Hajime Matsushita
发明人： Katsuya Matsumoto , Takashi Ebata , Koshi Koseki , Koji Okano , Hiroshi Kawakami , Hajime Matsushita
IPC分类号： C07D301/02 , C07D301/03 , C07D301/24 , C07D303/04 , C07D493/04 , C07D493/08 , C07D493/18 , C07H3/10 , C07D407/14 , C07D407/02
CPC分类号： C07D301/14 , C07D301/02 , C07D301/24 , C07D303/04 , C07D493/04 , C07D493/08 , C07H3/10
摘要： There is provided a method of preparing an epoxide (1a) or (1b) shown below: ##STR1## where R.sup.1, R.sup.2, R.sup.3, and R.sup.4 represent a hydrogen atom, an alkyl group, an alkenyl group, an aryl group, an alkoxy group, an aryloxy group, an acyl group, an alkyloxycarbonyl group, an aryloxycarbonyl group, allalkyl group, a silyl group, and a silyloxy group; the groups may be bonded with each other to form rings in the case where these groups can be bivalent; these groups may be the same or different, may have substituting groups, or may be branched; and each form (isomer) has a structure in which one side of the plane constituted by double bonds, R.sup.1, R.sup.2, R.sup.3 and R.sup.4, is more seterically hindered in comparison with the other side;characterized in that:an olefin represented by the formula (2) below, is reacted with iodine in the presence of compound generating acyloxy ion, ##STR2## where R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are the same as defined above; and then the reaction mixture is treated in the presence of a base, thereby forming an oxirane ring stereoselectively on the more sterically hindered side of the olefin.
摘要翻译： PCT No.PCT / JP93 / 00648 Sec。 371日期：1993年12月30日 102（e）日期1993年12月30日PCT提交1993年5月18日PCT公布。公开号WO93 / 23387 （1a）或（1b）的制备方法：其中R 1，R 2，R 3和R 4表示氢原子，原子，烷基，烯基，芳基，烷氧基，芳氧基，酰基，烷氧基羰基，芳氧基羰基，全烷基，甲硅烷基和甲硅烷氧基; 在这些基团可以是二价的情况下，基团可以彼此键合形成环; 这些基团可以相同或不同，可以具有取代基团，或者可以是支链基团; 并且每种形式（异构体）具有其中由双键R1，R2，R3和R4构成的平面的一侧与另一侧相比更受阻碍的结构; 其特征在于：下述式（2）表示的烯烃与碘反应，生成酰氧基的化合物存在下，与上述相同; 然后在碱的存在下处理反应混合物，从而立体选择性地在烯烃的空间位阻侧上形成环氧乙烷环。

3. 发明授权

US5391769A Method of preparing 3-DPA-lactone 失效
标题翻译：制备3-DPA-内酯的方法
公开(公告)号：US5391769A
公开(公告)日：1995-02-21
申请号：US987277
申请日：1993-03-10
申请人： Katsuya Matsumoto , Takashi Ebata , Hiroshi Kawakami , Koshi Koseki , Hajime Matsushita
发明人： Katsuya Matsumoto , Takashi Ebata , Hiroshi Kawakami , Koshi Koseki , Hajime Matsushita
IPC分类号： C07D307/33 , C07D307/60 , C07D305/12
CPC分类号： C07D307/33 , C07D307/60 , Y02P20/55
摘要： The present invention discloses a method of preparing 3-DPA-lactone, which is difficult to obtain in a large amount from nature. According to the method of the present invention, the target compound can be synthesized at a high yield in fewer steps and more easily than by the conventional synthesizing technique, and selectively from a widely available material. In the method of the present invention, the hydroxyl groups at the 2- and 5 -positions of .gamma.-ribonolactone are protected, and then the hydroxyl group at the 3-position is eliminated so as to form a double bond between the 2- and 3-positions. After that, the protecting groups for the hydroxyl groups are eliminated.
摘要翻译： PCT No.PCT / JP92 / 00925 Sec。 371日期1993年3月10日 102（e）1993年3月10日PCT提交1992年7月21日PCT公布。出版物WO93 / 02070 日期：1993年2月4日。本发明公开了一种难以从大自然中获得大量的3-DPA-内酯的方法。根据本发明的方法，目标化合物可以较少的步骤以较高的收率合成，并且比常规的合成技术更容易地合成，并且可以从广泛使用的材料中选择性地合成。在本发明的方法中，γ-葡聚内酯的2位和5位上的羟基被保护，然后除去3-位上的羟基，以形成2-和 3个职位。之后，除去羟基的保护基。

4. 发明授权

US5416204A Method for preparing 2'-3'-dideoxy-.beta.-nucleosides using 2,2-dideoxy-di(organothio)-pentofuranose intermediates 失效
标题翻译：使用2,2-二脱氧 - 二（有机硫） - 呋喃糖苷中间体制备2'-3'-二脱氧-β-核苷的方法
公开(公告)号：US5416204A
公开(公告)日：1995-05-16
申请号：US971768
申请日：1993-02-12
申请人： Hiroshi Kawakami , Katsuya Matsumoto , Koshi Koseki , Takashi Ebata , Hajime Matsushita , Kazuo Itoh , Yoshitake Naoi
发明人： Hiroshi Kawakami , Katsuya Matsumoto , Koshi Koseki , Takashi Ebata , Hajime Matsushita , Kazuo Itoh , Yoshitake Naoi
IPC分类号： C07D405/04 , C07F7/18 , C07H19/06 , C07H19/073 , C07H1/00
CPC分类号： C07D405/04 , C07F7/1856 , C07H19/06 , Y02P20/55
摘要： 2,3-Dideoxy-2,2-di(organothio)-B-D-pentofuranosyl-pyrimidines are disclosed as intermediates in the synthesis of 2', 3'-dideoxynucleosides and have the structure shown below. ##STR1## wherein R.sup.4 is a hydroxyl protecting group;X is oxygen or nitrogen, said nitrogen being bonded to a hydrogen atom, an alkyl or acyl group;Y is hydrogen, halogen, alkyl, haloalkyl or haloalkenyl; andR.sup.5 is alkyl, aralkyl, or aryl wherein aralkkyl or aryl is substituted with hydrogen, halogen, nitro or alkoxy.2', 3'-Dideoxynucleosides, products of the above intermediates, are useful as antiviral agents.
摘要翻译： PCT No.PCT / JP92 / 00752 Sec。 371日期：1993年2月12日 102（e）日期1993年2月12日PCT提交1992年6月12日PCT公布。公开号WO92 / 22548 1992年12月23日的日期.2,3-二脱氧-2,2-二（有机硫）-B-D-呋喃鸟糖基 - 嘧啶作为2'，3'-双脱氧核苷合成中的中间体被公开，具有如下结构。其中R 4是羟基保护基; X是氧或氮，所说的氮键合到氢原子，烷基或酰基上; Y是氢，卤素，烷基，卤代烷基或卤代烯基; R 5为烷基，芳烷基或芳基，其中芳烷基或芳基被氢，卤素，硝基或烷氧基取代。 2'，3'-双脱氧核苷，上述中间体的产物可用作抗病毒剂。

5. 发明授权

US5412111A Method of preparing (3R,4R)-3-hydroxy-4-hydroxymethyl-4-butanolide 失效
标题翻译：制备（3R，4R）-3-羟基-4-羟甲基-4-丁醇酯的方法
公开(公告)号：US5412111A
公开(公告)日：1995-05-02
申请号：US095182
申请日：1993-07-23
申请人： Katsuya Matsumoto , Takashi Ebata , Koshi Koseki , Koji Okano , Hiroshi Kawakami , Hajime Matsushita
发明人： Katsuya Matsumoto , Takashi Ebata , Koshi Koseki , Koji Okano , Hiroshi Kawakami , Hajime Matsushita
IPC分类号： C07D307/33 , C07D493/04 , C07D493/08 , C07D493/18 , C07H3/10
CPC分类号： C07D307/33 , C07D493/08 , C07H3/10
摘要： Providing a method of preparing (3R,4R)-3-hydroxy-4-hydroxymethyl-4-butanolide conveniently and selectively from a widely available raw material in a high yield. A carbonyl group of the 2-position of levoglucosenone is reduced to obtain a hydroxyl group of a .beta.-configuration. Then, an iodo-group of an .alpha.-configuration and an acyloxy ion of a .beta.-configuration are introduced regioselectively and stereoselectively to the double bond at the 4-position and the 3-position of the above-mentioned levoglucosenone, respectively, keeping a trans stereochemical relationship. An alkoxide is then formed, by hydrolysis and an oxirane ring of a .beta.-configuration is formed by removing an iodo-group by intramolecular nucleophilic displacement reaction of the alkoxide. After the hydroxyl group of the 2-position is oxidized to convert to a carbonyl group, the oxirane ring is reductively and selectively cleaved, thereby obtaining a chemical compound having no substituent at the 3-position and a hydroxyl group of a .beta.-configuration at the 4-position. Finally a lactone of 5-membered-ring is prepared by subjecting the above-obtained compound to Baeyer-Villigar oxidation.
摘要翻译：提供从广泛获得的原料中以高产率方便且有选择地制备（3R，4R）-3-羟基-4-羟甲基-4-丁醇的方法。缩合左旋葡萄糖酮的2-位的羰基，得到β-构型的羟基。然后，分别对上述左旋葡萄糖酮的4-位和3-位分别选择性且立体选择地引入α-构型的碘组和β-构型的酰氧基，保持反式立体化学关系。然后通过水解形成醇盐，通过醇盐的分子内亲核取代反应除去碘基形成β-构型的环氧乙烷环。在2-位的羟基被氧化转化成羰基之后，环氧乙烷环被还原和选择性地裂解，从而得到在3-位没有取代基的化合物和β-构型的羟基在 4位。最后通过将上述得到的化合物进行Baeyer-Villigar氧化来制备5元环的内酯。

6. 发明授权

US5468881A Method of producing cis-whiskey lactone 失效
标题翻译：顺式威士忌内酯的制备方法
公开(公告)号：US5468881A
公开(公告)日：1995-11-21
申请号：US920578
申请日：1992-08-27
申请人： Takashi Ebata , Katsuya Matsumoto , Koshi Koseki , Hiroshi Kawakami , Hajime Matsushita , Hajime Yoshikoshi , Masakazu Okaniwa
发明人： Takashi Ebata , Katsuya Matsumoto , Koshi Koseki , Hiroshi Kawakami , Hajime Matsushita , Hajime Yoshikoshi , Masakazu Okaniwa
IPC分类号： C07D307/33 , C07D315/00 , C07D307/02
CPC分类号： C07D307/33 , C07D315/00
摘要： After the lactone portion of trans-whiskey lactone is hydrolyzed with potassium hydroxide, this portion is reacted with isopropyl bromide and mixed with an alkyl group, thereby obtaining isopropyl (3S,4S)-4-hydroxy-3-methyloctanoate. Then, the isopropyl (3S,4S)-4-hydroxy-3-methyloctanoate is reacted with diethyl azodicarboxylate in the presence of triphenylphosphine and azodicarboxylate, thereby obtaining isopropyl (3S,4S)-4-(3',5'-dinitrobenzoyloxy)-3-methyloctanoate. The isopropyl (3S,4S)-4-(3',5'-dinitrobenzoyloxy)-3-methyloctanoate is hydrolyzed in 2% potassium hydroxide, and as a result, cis-whiskey lactone (A) represented by the following general formula is obtained. According to this method, cis-whiskey lactone, one of the perfume components of whiskey and wine, can be produced selectively and easily. ##STR1##
摘要翻译： PCT No.PCT / JP91 / 01780 Sec。 371日期：1992年8月27日 102（e）日期1992年8月27日PCT 1991年12月27日PCT PCT。 WO92 / 12143 PCT出版物日期：1992年7月23日。反式威士忌内酯的内酯部分用氢氧化钾水解后，将该部分与异丙基溴反应并与烷基混合，从而得到异丙基（3S，4S）-4-羟基-3 - 甲基辛酸酯。然后，将（3S，4S）-4-羟基-3-甲基辛酸异丙酯与偶氮二羧酸二乙酯在三苯基膦和偶氮二羧酸酯存在下反应，得到异丙基（3S，4S）-4-（3'，5'-二硝基苯甲酰氧基） -3-甲基辛酸酯。异丙基（3S，4S）-4-（3'，5'-二硝基苯甲酰氧基）-3-甲基辛酸酯在2％氢氧化钾中水解，结果得到下述通式所示的顺式 - 威士忌内酯（A）获得。根据该方法，可以选择性且容易地制备顺式威士忌内酯，威士忌酒和葡萄酒的香料成分之一。（A）

7. 发明授权

US5284973A Method of preparing an acid additional salt of delta-aminolevulinic acid 失效
标题翻译：制备δ-氨基乙酰丙酸酸添加盐的方法
公开(公告)号：US5284973A
公开(公告)日：1994-02-08
申请号：US73613
申请日：1993-06-08
申请人： Takashi Ebata , Hiroshi Kawakami , Katsuya Matsumoto , Koshi Koseki , Hajime Matsushita
发明人： Takashi Ebata , Hiroshi Kawakami , Katsuya Matsumoto , Koshi Koseki , Hajime Matsushita
IPC分类号： C07C227/02 , C07C229/22 , C07C229/00
CPC分类号： C07C229/22 , C07C227/02 , Y02P20/55
摘要： An acid addition salt of .delta.-aminolevulinic acid is prepared in such a way that tetrahydrofurfurylamine (VI) is reacted with phthalic anhydride under an anhydrous condition to introduce a phthal group which protects amino group of tetrahydrofurfurylamine to give N-tetrahydrofurfuryl phthalimide (III), carbon atoms of the first- and fourth-positions of thus obtained N-tetrahydrofurfurylphthalimide (III) are oxidized at 80.degree. C. using sodium periodate as a oxidizing agent and ruthenium chloride hydrate as a catalyst to yield 5-phthalimidolevulinic acid (II), then the protecting group of 5-phthalimidolevulinic acid (II) is deprotected using an acid to prepare an acid additional salt of .delta.-aminolevulinic acid. The acid additional salt of .delta.-aminolevulinic acid is readily converted by neutralization by an alkali to .delta.-aminolevulinic acid, which is very useful as a precursor of Vitamin B.sub.12, heme and chlorophyll.
摘要翻译：制备δ-氨基乙酰丙酸的酸加成盐，使四氢糠胺（VI）在无水条件下与邻苯二甲酸酐反应，引入保护四氢糠胺氨基的邻苯基基团，得到N-四氢糠基邻苯二甲酰亚胺（III），由此获得的N-四氢糠基邻苯二甲酰亚胺（III）的第一和第四位的碳原子在80℃下用高碘酸钠作为氧化剂和氯化钌水合物作为催化剂氧化，得到5-苯二酰亚氨基乙酰丙酸（II），然后使用酸去保护5-苯二甲酰亚氨基乙酰丙酸（II）的保护基，以制备δ-氨基乙酰丙酸的酸另外的盐。 δ-氨基乙酰丙酸的酸附加盐通过碱中和而容易地转化为δ-氨基乙酰丙酸，其作为维生素B12，血红素和叶绿素的前体非常有用。

8. 发明授权

US5374744A Method for manufacturing 4-substituted-Y-lactone and novel substance 失效
标题翻译：制备4-取代的Y-内酯和新物质的方法
公开(公告)号：US5374744A
公开(公告)日：1994-12-20
申请号：US937848
申请日：1992-10-21
申请人： Koshi Koseki , Hiroshi Kawakami , Takashi Ebata , Hajime Matsushita , Mikio Ono
发明人： Koshi Koseki , Hiroshi Kawakami , Takashi Ebata , Hajime Matsushita , Mikio Ono
IPC分类号： C07D307/33 , C07D307/58 , C07D315/00 , C07D307/28
CPC分类号： C07D307/33 , C07D307/58 , C07D315/00
摘要： An alkynyl group having a triple bond at the carbon atom at the 1-position is introduced to a carbon atom at the 1-position of 2,3-O-isopropylidene-D-ribofuranose. The diol part is then cleaved to obtain a lactol compound. This lactol compound is oxidized to obtain a lactone compound. The ketal part of the lactone compound is hydrolyzed and the compound is further subjected to a reduction reaction. The hydroxyl groups at the 2- and 3-positions are then eliminated, and the double bond between the 2- and 3-positions of the resultant compound is reduced to obtain a 4-substituted-.gamma.-lactone.
摘要翻译： PCT No.PCT / JP92 / 00150 Sec。 371日期：1992年10月21日 102（e）日期1992年10月21日PCT提交1992年2月17日PCT公布。出版物WO92 / 14720 PCT 日期：1992年3月9日。在1位碳原子上具有三键的炔基被引入2,3-O-异亚丙基-D-呋喃核糖1位的碳原子上。然后将二醇部分切割以获得内酯化合物。将该内酯化合物氧化，得到内酯化合物。内酯化合物的缩酮部分被水解，化合物进一步进行还原反应。然后除去2-和3-位的羟基，并将所得化合物的2-和3-位之间的双键还原，得到4-取代-γ-内酯。

9. 发明授权

US5216177A Method of preparing trans-3,4-disubstituted-.gamma.-lactones 失效
标题翻译：制备TRANS-3,4-DISUBSTITUTED-（GAMMA）-LACTONES的方法
公开(公告)号：US5216177A
公开(公告)日：1993-06-01
申请号：US695010
申请日：1991-05-03
申请人： Takashi Ebata , Hajime Matsushita , Hiroshi Kawakami , Koshi Koseki
发明人： Takashi Ebata , Hajime Matsushita , Hiroshi Kawakami , Koshi Koseki
IPC分类号： C07D307/33 , C07D315/00 , C07D493/08
CPC分类号： C07D315/00
摘要： First, levoglucosenone is made to react with methyl lithium in the presence of copper iodide in order to introduce a methyl group into an enone group of levoglucosenone, and to obtain 1,6-anhydro-3,4-dideoxy-4-C-methyl-.beta.-D-erythro-hexopyranose-2-ulose. This methyl compound is oxidized in acetic acid for lactone formation, and (3S,4S)-5-hydroxy-3-methylpentan-4-olide is thus obtained. Further, this lactone is made to react with tosyl chloride in anhydrous pyridine to obtain (3S,4S)-3-methyl-5-tosyloxypentan-4-olide (tosylate). The obtained tosylate is alkylated with n-propyl lithium in the presence of copper iodide to obtain (3S,4R)-3-methyl-4-octanolide. Here, the (3S,4S)-3-methyl-5-tosyloxypentan-4-olide may be treated with potassium carbonate to cleave lactone ring once, thereby obtaining epoxide. After that, the obtained epoxide is alkylated to form lactone ring again to obtain (3S,4R)-3-methyl-4-octanolide.

10. 发明授权

US5112994A Method of producing (S)-4-hydroxymethyl-.gamma.-lactone 失效
标题翻译：制备（S）-4-羟基甲基 - （氨基）-L-酮的方法
公开(公告)号：US5112994A
公开(公告)日：1992-05-12
申请号：US583647
申请日：1990-09-17
申请人： Koshi Koseki , Takashi Ebata , Hiroshi Kawakami , Hajime Matsushita , Kazuo Itoh , Yoshitake Naoi
发明人： Koshi Koseki , Takashi Ebata , Hiroshi Kawakami , Hajime Matsushita , Kazuo Itoh , Yoshitake Naoi
IPC分类号： C07D307/33 , C07D493/08
CPC分类号： C07D307/33 , C07D493/08
摘要： (S)-4-hydroxymethyl-.gamma.-lactone is prepared by oxidizing dihydrolevoglucosenone with a peracid in an organic solvent. (S)-4-hydroxymethyl-.gamma.-lactone is prepared from levoglucosenone. First, levoglucosenone is catalytic hydrogenated, thereby dihydrolevoglucosenone is obtained. Next, dihydrolevoglucosenone thus obtained is oxidized with a peracid in an organic solvent, thereby (S)-4-hydroxymethyl-.gamma.-lactone is obtained. In this manner, (S)-4-hydroxymethyl-.gamma.-lactone can be obtained with high optical purity.

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