Application of Chemoselective Pancreatin Powder-Catalyzed Deacetylation Reaction in the Synthesis of Key Statin Side Chain Intermediate (4R,6X)-4-(tert-Butyldimethylsilyloxy)-6-(hydroxymethyl)tetrahydropyran-2-one

Vincent Troiani; Jerome Cluzeau; Zdenko Casar

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Application of Chemoselective Pancreatin Powder-Catalyzed Deacetylation Reaction in the Synthesis of Key Statin Side Chain Intermediate (4R,6X)-4-(tert-Butyldimethylsilyloxy)-6-(hydroxymethyl)tetrahydropyran-2-one

机译：化学选择性胰酶粉末催化的脱乙酰反应在关键他汀侧链中间体（4R，6X）-4-（叔丁基二甲基甲硅烷氧基）-6-（羟甲基）四氢吡喃-2-酮的合成中的应用

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A chemoselective biocatalytic procedure for the synthesis of (4R,6S)-4-(terr-butyldimethylsilyloxy)-6-(hydroxy-methyl)tetrahydro-2H-pyran-2-one, a key lactonized statin side chain intermediate, from its acetate precursor is described. The presented method is based on the pancreatin powder-catalyzed cleavage of the acetyl group in ((2S,4R)-4-(tert-butyldi-methylsilyloxy)-6-oxotetrahydro-2H-pyran-2-yl)methyl acetate. The reaction was conducted in aqueous medium. The overall process is performed in a convenient way and economical manner suitable for industrial use.

机译：化学选择性生物催化程序，由其乙酸酯合成（4R，6S）-4-（叔丁基二甲基甲硅烷氧基）-6-（羟基甲基）四氢-2H-吡喃-2-酮（一种关键的内酯化他汀类侧链中间体）描述了前体。提出的方法是基于胰酶粉催化的（（2S，4R）-4-（叔丁基二甲基甲硅烷氧基）-6-氧四氢-2H-吡喃-2-基）乙酸甲酯中乙酰基的裂解。反应在水性介质中进行。整个过程以适合工业用途的方便的方式和经济的方式进行。

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《Organic process research & development》 |2011年第3期|共9页
作者
Vincent Troiani; Jerome Cluzeau; Zdenko Casar;
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1. Application of Chemoselective Pancreatin Powder-Catalyzed Deacetylation Reaction in the Synthesis of Key Statin Side Chain Intermediate (4R,6X)-4-(tert-Butyldimethylsilyloxy)-6-(hydroxymethyl)tetrahydropyran-2-one [J] . Vincent Troiani, Jerome Cluzeau, Zdenko Casar Organic process research & development . 2011,第3期

机译：化学选择性胰酶粉末催化的脱乙酰反应在关键他汀侧链中间体（4R，6X）-4-（叔丁基二甲基甲硅烷氧基）-6-（羟甲基）四氢吡喃-2-酮的合成中的应用
2. Calorimetric Insight into Coupling between Functionalized Primary Alkyl Halide and Vinylic Organocuprate Reagent:Experimental Determination of Reaction Enthalpies in the Synthesis of (R)-Ethyl 3-(tert-butyldimethylsilyloxy) hex-5-enoate - a Key Lactonized Statin Side Chain Precursor [J] . Zdenko Casar, Marko Tramsek, Andreja Gorsek Acta Chimica Slovenica . 2010,第1期

机译：量热法研究功能化伯烷基卤与乙烯型有机戊酸酯试剂之间的偶联：（R）-3-（叔丁基二甲基甲硅烷氧基）己-5-烯酸乙酯的合成中反应焓的实验确定
3. Enantioselective Synthesis of Benzyl (1S,2R,4R)-4-(tert-Butoxycarbonylamino)-2-(hydroxymethyl)-cyclohexylcarbamate Using an Iodolactamization As the Key Step [J] . Soo S. Ko, Matthew E. Voss, Percy H. Carter, The Journal of Organic Chemistry . 2009,第16期

机译：以碘内酰胺化为关键步骤对苯甲酸（1S，2R，4R）-4-（叔丁氧基羰基氨基）-2-（羟甲基）-环己基氨基甲酸酯的对映选择性合成
4. A Highly Productive Whole-Cell DERA Chemoenzymatic Process for Production of Key Lactonized Side-Chain Intermediates in Statin Synthesis [O] . Matej Ošlaj, Jérôme Cluzeau, Damir Orkić, -1

机译：高生产效率的全细胞DERA化学酶法用于生产他汀合成中的关键亮化侧链中间体
5. A highly productive, whole-cell DERA chemoenzymatic process for production of key lactonized side-chain intermediates in statin synthesis. [O] . Matej Ošlaj, Jérôme Cluzeau, Damir Orkić, 2013

机译：一种高产的全细胞DERa化学酶法，用于生产他汀类药物合成中的关键内酯化侧链中间体。

Application of Chemoselective Pancreatin Powder-Catalyzed Deacetylation Reaction in the Synthesis of Key Statin Side Chain Intermediate (4R,6X)-4-(tert-Butyldimethylsilyloxy)-6-(hydroxymethyl)tetrahydropyran-2-one

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