Synthesis of BACE Inhibitor LY2886721. Part I. An Asymmetric Nitrone Cycloaddition Strategy

Kolis Stanley P.; Hansen Marvin M.; Arslantas Enver; Braendli Lukas; Buser Jonas; DeBaillie Amy C.; Frederick Andrea L.; Hoard David W.; Hollister Adrienne; Huber Dominique; Kull Thomas; Linder Ryan J.; Martin Thomas J.; Richey Rachel N.; Stutz Alfred; Waibel Michael; Ward Jeffrey A.; Zamfir Alexandru

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Synthesis of BACE Inhibitor LY2886721. Part I. An Asymmetric Nitrone Cycloaddition Strategy

机译：BACE抑制剂LY2886721。的合成第一部分：不对称氮杂环加成策略

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A scalable, asymmetric synthesis of (3aS,6aS)-6a-(5-bromo-2-fluorophenyl)-1-((R)-1-phenylpropyl)tetrahydro-1H,3H-furo[3,4-c]isoxazole, a key intermediate in the synthesis of LY2886721, is reported Highlights of the synthesis include the development of an asymmetric [3 + 2] intramolecular cycloaddition facilitated by trifluoroethanol, and the development of a new synthesis of (R)-N-(1-phenylpropyl)hydroxylamine tosylate which proceeds through a p-anisaldehyde imine and avoids the formation of toxic hydrogen cyanide gas as a byproduct. The synthesis proceeds over four steps and provides the product in 36% overall yield.

机译：（3aS，6aS）-6a-（5-溴-2-氟苯基）-1-（（R）-1-苯丙基）四氢-1H，3H-呋喃[3,4-c]异恶唑的可扩展，不对称合成据报道，它是LY2886721合成中的关键中间体，其合成亮点包括开发由三氟乙醇促进的不对称[3 + 2]分子内环加成反应，以及开发新的（R）-N-（1-苯丙基）羟胺甲苯磺酸盐通过对茴香醛亚胺生成，避免形成有毒的氰化氢副产物。合成过程分四个步骤进行，提供的产品收率为36％。

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《Organic process research & development》 |2015年第9期|共11页
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Kolis Stanley P.; Hansen Marvin M.; Arslantas Enver; Braendli Lukas; Buser Jonas; DeBaillie Amy C.; Frederick Andrea L.; Hoard David W.; Hollister Adrienne; Huber Dominique; Kull Thomas; Linder Ryan J.; Martin Thomas J.; Richey Rachel N.; Stutz Alfred; Waibel Michael; Ward Jeffrey A.; Zamfir Alexandru;
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1. Synthesis of BACE Inhibitor LY2886721. Part I. An Asymmetric Nitrone Cycloaddition Strategy [J] . Kolis Stanley P., Hansen Marvin M., Arslantas Enver, Organic process research & development . 2015,第9期

机译：BACE抑制剂LY2886721。的合成第一部分：不对称氮杂环加成策略
2. Synthesis of BACE Inhibitor LY2886721. Part II. Isoxazolidines as Precursors to Chiral Aminothiazines, Selective Peptide Coupling, and a Controlled Reactive Crystallization [J] . Hansen Marvin M., Jarmer Daniel J., Arslantas Enver, Organic process research & development . 2015,第9期

机译：BACE抑制剂LY2886721。的合成第二部分异恶唑烷作为手性氨基噻嗪的前体，选择性肽偶联和可控的反应结晶
3. Synthesis and Asymmetric [3 + 2] Cycloaddition Reactions of Chiral Cyclic Nitrone: A Novel System Providing Maximal Facial Bias for both Nitrone and Dipolarophile [J] . Teruhiko Ishikawa, Yoshiaki Tajima, Miyuki Fukui, Angewandte Chemie . 1996,第16期

机译：手性环硝基的合成和不对称[3 + 2]环加成反应：一种新型系统，可为硝基和双极性亲子提供最大的面部偏倚
4. Copper(II)-Bis(oxazolme)-Cataryzed Asymmetric 1,3-Dipolar Cycloadditions of Nitrones with 2-Alkenoyl Pyridine N-Oxides [C] . Santiago Barroso, Gonzalo Blay, Luz Cardona European Symposium on Organic Chemistry . 2009

机译：铜（II） - 甲磺酸（Oxazolme） - 用2-链烯酰吡啶N-氧化物的硝基甘氨酸的不对称1,3-偶极环加入
5. Tandem cycloaddition chemistry: Part I. Synthesis and crystallographic analysis of 1-azafenestranes. Part II. Synthesis and reactivity of N-vinyl nitrones [D] . Montgomery, Justin 2006

机译：串联环加成化学：第一部分。1-氮杂苯甲酮的合成和晶体学分析。第二部分N-乙烯基硝酮的合成与反应性
6. A Nitrone Dipolar Cycloaddition Strategy toward an Enantioselective Synthesis of Massadine [O] . Jeffrey S. Cannon -1

机译：Nitrone偶极环加成策略对马萨丁的对映选择性合成。
7. Stereoselective 1,3-dipolar cycloadditions of nitrones derived from amino acids. Asymmetric synthesis of N-(alkoxycarbonylmethyl)-3-hydroxypyrrolidin-2-ones [O] . Merino Pedro, Greco Graziella, Tejero Tomás, 2015

机译：衍生自氨基酸的硝酮的立体选择性1,3-偶极环加成。 N-（烷氧羰基甲基）-3-羟基吡咯烷酮-2-酮的不对称合成

Synthesis of BACE Inhibitor LY2886721. Part I. An Asymmetric Nitrone Cycloaddition Strategy

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