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1. 发明授权

US5194637A Method and apparatus for synthesis of highly isomerically pure stereoisomers of glycidol derivatives 失效
标题翻译：合成GLYCIDO衍生物的高纯度异构体纯度的方法和装置
公开(公告)号：US5194637A
公开(公告)日：1993-03-16
申请号：US748672
申请日：1991-08-22
申请人： Roger C. Hahn
发明人： Roger C. Hahn
IPC分类号： C07C309/71 , C07D303/16
CPC分类号： C07D303/16 , C07C309/71 , C07C2102/42
摘要： Methods are provided for producing isomerically enriched camphorsulfonates, and in particular a diastereomerically enriched glycidyl camphorsulfonate by bromide-casylate exchange between an alkyl casylate and the bromide analog of the desired casylate, followed by separation of a higher melting diastereomer by selective recrystallization. There is also shown the production of a desired casylate by reacting a racemic or enantiomerically enriched arenesulfonate with a quaternary casylate. Randomization and recycling of an isomerically enriched casylate is provided by reaction with an achiral bromide analog in the presence of a quaternary salt. Specially adapted apparatus for conducting the randomization reaction is provided. There is also shown a process for producing an alkyl casylate by the reaction of a metal casylate and a quaternary casylate with a trialkyl phosphite in the presence of a slight molar excess of sulfuric acid.
摘要翻译：提供了用于通过溴代 - 甲酸酯交换甲磺酸烷基酯和所需的甲磺酸酯的溴化物类似物之间产生异构体富集的樟脑磺酸盐，特别是非对映异构体富集的樟脑磺缩水甘油基缩水甘油酯的方法，然后通过选择性重结晶分离出较高熔点的非对映异构体。还显示通过使外消旋或对映异构体富集的芳烃磺酸盐与季铵化合物反应制备所需的甲酸酯。通过在季盐的存在下与非手性溴化物类似物反应来提供异构体富集的甲酸酯的随机化和再循环。提供了用于进行随机化反应的专用设备。还显示了在稍微摩尔过量的硫酸存在下，通过金属甲酸酯和季铵化合物与亚磷酸三烷基酯的反应制备烷基酯化的方法。

2. 发明授权

US5274160A Method and apparatus for synthesis of highly isomerically pure stereoisomers of glycidol derivatives 失效
标题翻译：用于合成缩水甘油衍生物的高度异构纯的立体异构体的方法和装置
公开(公告)号：US5274160A
公开(公告)日：1993-12-28
申请号：US4923
申请日：1993-01-15
申请人： Roger C. Hahn
发明人： Roger C. Hahn
IPC分类号： C07C309/71 , C07D303/16 , C07D301/00 , C07D301/32
CPC分类号： C07C309/71 , C07D303/16 , C07C2102/42
摘要： There is disclosed a process for producing an alkyl casylate by the reaction of a metal casylate or an enantiomer of a quaternary casylate with a trialkyl phosphite in the presence of a slight molar excess of sulfuric acid. According to one aspect of the invention the reaction is conducted under heat in the presence of concentrated sulfuric acid. When the reaction is complete, an organic layer that contains the alkyl casylate is isolated. In another aspect of the invention at least 1.0 equivalents of a trialkyl phosphite is added to a thoroughly dried enantiomer of camphorsulfonic acid, and the mixture optionally heated to about 80.degree. C. The reaction is allowed to proceed until camphorsulfonic acid is no longer present. Thereafter all phosphorus-containing species are selectively removed by distillation at reduced pressure to obtain a pure alkyl casylate in high yield.
摘要翻译：公开了在少量摩尔过量的硫酸的存在下，通过金属甲酸酯或季戊烯酸酯与三烷基亚磷酸酯的对映异构体的反应制备烷基酯化的方法。根据本发明的一个方面，反应在加热下在浓硫酸的存在下进行。当反应完成时，分离含有芳基酯的有机层。在本发明的另一方面，将至少1.0当量的亚磷酸三烷基酯加入到樟脑磺酸的彻底干燥的对映异构体中，并将混合物任选地加热至约80℃。使反应进行直到樟脑磺酸不再存在。此后，通过减压蒸馏选择性地除去所有含磷物质，以高产率得到纯的烷基酯。

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