Reagent‐Controlled α‐Selective Dehydrative Glycosylation of 2,6‐Dideoxy‐ and 2,3,6‐Trideoxy Sugars |
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| Authors: | Dr. Jason M. Nogueira Marissa Bylsma Danielle K. Bright Prof. Clay S. Bennett |
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| Affiliation: | Department of Chemistry, Tufts University, Medford, MA, USA |
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| Abstract: | We have found that activating either 2,3‐bis(2,3,4‐trimethoxyphenyl)cyclopropenone or 2,3‐bis(2,3,4‐trimethoxyphenyl)cyclopropene‐1‐thione with oxalyl bromide results in the formation of a species that promotes the glycosylation between 2,6‐dideoxy‐sugar hemiacetals and glycosyl acceptors in good yield and high α‐selectivity. Both reactions are mild and tolerate a number of sensitive functional groups including highly acid‐labile 2,3,6‐trideoxy‐sugar linkages. |
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| Keywords: | carbohydrates diastereoselectivity glycosylation oligosaccharides synthetic methods |
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