One pot oxidative dehydration - oxidation of polyhydroxyhexanal oxime to polyhydroxy oxohexanenitrile: A versatile methodology for the facile access of azasugar alkaloids

Khobare Sandip R.; Gajare Vikas; Reddy E. Vishnuvardhan; Datrika Rajender; Banda Malavika; Siddaiah Vidavalur; Pachore Sharad S.; Timanna Upadhya; Dahanukar Vilas H.; Kumar U. K. Syam

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One pot oxidative dehydration - oxidation of polyhydroxyhexanal oxime to polyhydroxy oxohexanenitrile: A versatile methodology for the facile access of azasugar alkaloids

机译：一锅氧化脱水-将多羟基己肟氧化为多羟基氧己腈：一种简便的氮杂糖生物碱获取方法

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A unique oxidative dehydration-oxidation of polyhydroxy-oxime (7) to the corresponding ketonitrile (8) in one pot is reported for the first time in carbohydrate literature. Key ketonitrile intermediate (8) upon palladium hydroxide mediated cascade reaction afforded 1-deoxynojirimycin (DNJ) 1b in moderate diastereoselectivity. The cascade reaction involves the conversion of nitrile to amine, heteroannulation, reduction of the imine and subsequent debenzylation to furnish the azasugars. This oxidative dehydration-oxidation and reductive heteroannulation methodology is successfully utilized for the total synthesis of 1-deoxynojirimycin (1b), miglitol (2) and miglustat (3). (C) 2016 Elsevier Ltd. All rights reserved.

机译：在碳水化合物文献中首次报道了多羟基肟（7）在相应的酮腈（8）中的独特氧化脱水氧化反应。在氢氧化钯介导的级联反应中，关键的乙腈中间体（8）以中等的非对映选择性提供了1-deoxynojirimycin（DNJ）1b。级联反应涉及腈转化为胺，杂环化，亚胺的还原和随后的脱苄基作用以提供氮杂糖。这种氧化脱水-氧化和还原异环化方法已成功用于1-deoxynojirimycin（1b），miglitol（2）和miglustat（3）的全合成。（C）2016 Elsevier Ltd.保留所有权利。

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《Carbohydrate research》 |2016年第null期|共6页
作者
Khobare Sandip R.; Gajare Vikas; Reddy E. Vishnuvardhan; Datrika Rajender; Banda Malavika; Siddaiah Vidavalur; Pachore Sharad S.; Timanna Upadhya; Dahanukar Vilas H.; Kumar U. K. Syam;
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正文语种 eng
中图分类有机化学;
关键词
Deoxynojirimycin; Miglitol; Miglustat; Alcohol oxidation amp; oxime dehydration; Cascade reaction; Reductive aminative cyclization;

机译：脱氧野rim霉素;米格列醇;米格司他;醇氧化肟肟脱水;级联反应;还原性胺化环化;

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1. One pot oxidative dehydration - oxidation of polyhydroxyhexanal oxime to polyhydroxy oxohexanenitrile: A versatile methodology for the facile access of azasugar alkaloids [J] . Khobare Sandip R., Gajare Vikas, Reddy E. Vishnuvardhan, Carbohydrate research . 2016,第Null期

机译：一锅氧化脱水-将多羟基己肟氧化为多羟基氧己腈：一种简便的氮杂糖生物碱获取方法
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One pot oxidative dehydration - oxidation of polyhydroxyhexanal oxime to polyhydroxy oxohexanenitrile: A versatile methodology for the facile access of azasugar alkaloids

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