A new synthesis of aryl mono C-glycosyl derivatives of dialdehyde sugars
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The Department of Chemistry seeks to provide students with a foundation in the fundamentals and application of chemical theories and processes of the lab. Thus prepared they me pursue careers as teachers, industry supervisors, or research chemists in a variety of domains (governmental, academic, etc).
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The Department of Chemistry was founded in 1880.
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1880-present
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- College of Liberal Arts and Sciences (parent college)
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Abstract
A new synthesis of mono C-glycosyl derivatives of dialdehyde sugars using a Michael additionlaldol condensation sequence has been developed. It is complementary to previously reported methods for the production of C-glycosyl compounds. The synthesis involves the Michael addition reaction of an enol silyl ether with acetylbenzoquinone followed by an aldol condensation and subsequent aromatization of the resulting hydroxy ketone. The aldol condensation proceeds only under select conditions and affords the unstable ketols 7 and 15.
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Reprinted (adapted) with permission from The Journal of Organic Chemistry, 55(16); 4922-4925. Doi: 10.1021/jo00303a031. Copyright 1990 American Chemical Society.