176380-03-3Relevant articles and documents
Mapping the Relationship between Glycosyl Acceptor Reactivity and Glycosylation Stereoselectivity
van der Vorm, Stefan,van Hengst, Jacob M. A.,Bakker, Marloes,Overkleeft, Herman S.,van der Marel, Gijsbert A.,Codée, Jeroen D. C.
, p. 8240 - 8244 (2018/05/03)
The reactivity of both coupling partners—the glycosyl donor and acceptor—is decisive for the outcome of a glycosylation reaction, in terms of both yield and stereoselectivity. Where the reactivity of glycosyl donors is well understood and can be controlled through manipulation of the functional/protecting-group pattern, the reactivity of glycosyl acceptor alcohols is poorly understood. We here present an operationally simple system to gauge glycosyl acceptor reactivity, which employs two conformationally locked donors with stereoselectivity that critically depends on the reactivity of the nucleophile. A wide array of acceptors was screened and their structure–reactivity/stereoselectivity relationships established. By systematically varying the protecting groups, the reactivity of glycosyl acceptors can be adjusted to attain stereoselective cis-glucosylations.
The synthesis of methyl-3-O-(β-D-fucopyranosyl)-β-D-quinovopyranoside and its 3′-O-, 2,3′-di-O-, and 2′,3′-di-O-methyl derivatives
Khatuntseva,Sherman,Shashkov,Dabrowski,Nifant'ev
, p. 205 - 210 (2007/10/03)
Methyl-3-O-(β-D-fucopyranosyl)-β-D-quinovopyranoside and its 3′-O-, 2,3′-di-O-, and 2′,3′-di-O-methyl derivatives were obtained by the regioselective Helferich glycosylation of methyl-2-O-benzyl-β-D-quinovopyranoside with the 2,3,4-tri-O-benzoyl-α-D-fucopyranosyl bromide followed by the methylation with diazomethane or methyl iodide.