Synthesis of Isoxazolin-5-one Glucosides by a Cascade Reaction

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• 作者：Tobias Becker ; Helmar G枚rls ; Gerhard Pauls ; Roland Wedekind ; Marco Kai ; Stephan H. von Reu脽 ; Wilhelm Boland
• 刊名：Journal of Organic Chemistry
• 出版年：2013
• 出版时间：December 20, 2013
• 年：2013
• 卷：78
• 期：24
• 页码：12779-12783
• 全文大小：277K
• 年卷期：v.78,no.24(December 20, 2013)
• ISSN：1520-6904

文摘

A novel synthetic route was developed for the construction of isoxazolin-5-one glucosides using a cascade reaction. An X-ray crystal structure analysis of a isoxazolin-5-one glucoside confirmed the structure and stereochemistry of the heterocycle. The properties of the 伪- and 尾-anomers of the isoxazolin-5-one glucosides were compared. The first synthesis of 2-[6鈥?(3鈥?nitropropanoyl)-尾-d-glucopyranosyl]-3-isoxazolin-5-one was realized by direct enzymatic esterification without need of further protective groups.