Selective anomeric acetylation of unprotected sugars in water

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Selective anomeric acetylation of unprotected sugars in water.

High yielding selective acetylation of only the anomeric hydroxyl of unprotected sugars is possible in aqueous solution using 2-chloro-1,3-dimethylimidazolinium chloride (DMC), thioacetic acid, and a suitable base. The reaction, which may be performed on a multi-gram scale, is stereoselective for sugars that possess a hydroxyl group at position-2, exclusively yielding the 1,2-trans products. Th...

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Glycosylation is an immensely important biological process and one that is highly controlled and very efficient in nature. However, in a chemical laboratory the process is much more challenging and usually requires the extensive use of protecting groups to squelch reactivity at undesired reactive moieties. Nonetheless, by taking advantage of the differential reactivity of the anomeric center, a...

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ژورنال

عنوان ژورنال: Chemical Science

سال: 2017

ISSN: 2041-6520,2041-6539

DOI: 10.1039/c6sc04667c