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Investigation of Glycosyl Nitrates as Building Blocks for Chemical Glycosylation.


ABSTRACT: Glycosyl nitrates are important synthetic intermediates in the synthesis of 2-amino sugars, 1,2-orthoesters or, more recently, 2-OH glucose. However, glycosyl nitrates have never been glycosidated. Presented herein is our first attempt to use glycosyl nitrates as glycosyl donors for O-glycosylation. Lanthanide triflates showed good affinity to activate the nitrate leaving group.

SUBMITTER: Wang T 

PROVIDER: S-EPMC6656396 | biostudies-literature | 2018 Dec

REPOSITORIES: biostudies-literature

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Investigation of Glycosyl Nitrates as Building Blocks for Chemical Glycosylation.

Wang Tinghua T   Singh Yashapal Y   Stine Keith J KJ   Demchenko Alexei V AV  

European journal of organic chemistry 20180913 47


Glycosyl nitrates are important synthetic intermediates in the synthesis of 2-amino sugars, 1,2-orthoesters or, more recently, 2-OH glucose. However, glycosyl nitrates have never been glycosidated. Presented herein is our first attempt to use glycosyl nitrates as glycosyl donors for <i>O</i>-glycosylation. Lanthanide triflates showed good affinity to activate the nitrate leaving group. ...[more]

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