title: Reagent-Controlled α-Selective Dehydrative Glycosylation of 2,6-Dideoxy- and 2,3,6-Trideoxy Sugars.
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.
authors.affiliation: Department of Chemistry, Tufts University, 62 Talbot Ave., Medford, MA, 02155, USA.
authors.forename: Jason M
authors.initials: JM
authors.lastname: Nogueira
authors.affiliation: Department of Chemistry, Tufts University, 62 Talbot Ave., Medford, MA, 02155, USA.
authors.forename: Marissa
authors.initials: M
authors.lastname: Bylsma
authors.affiliation: Department of Chemistry, Tufts University, 62 Talbot Ave., Medford, MA, 02155, USA.
authors.forename: Danielle K
authors.initials: DK
authors.lastname: Bright
authors.affiliation: Department of Chemistry, Tufts University, 62 Talbot Ave., Medford, MA, 02155, USA. clay.bennett@tufts.edu.
authors.forename: Clay S
authors.identifier: 0000-0001-8070-4988
authors.initials: CS
authors.lastname: Bennett
keywords: carbohydrates; diastereoselectivity; glycosylation; oligosaccharides; synthetic methods