725228-65-9Relevant academic research and scientific papers
Synthesis of Glucuronoxylan Hexasaccharides by Preactivation-Based Glycosylations
B?hm, Maximilian,Madsen, Robert,Underlin, Emilie N.,d'Errico, Clotilde
, (2020/05/16)
The synthesis of two glucuronoxylans is described, which both consist of a pentaxylan backbone and a glucuronic acid linked to the 2 position in the fourth xylose residue from the reducing end. The two target molecules differ in the 4 position of the glucuronic acid where one is unsubstituted while the other contains a methyl ether. The pentaxylan backbone is assembled in four glycosylation reactions with phenyl thioglycoside donors. The couplings are performed by preactivation of the donor with in-situ-generated p-nitrobenzenesulfenyl triflate prior to addition of the acceptor. The glucuronic acids are then attached by Koenigs-Knorr glycosylations followed by deprotections. The syntheses employ a total of 8 steps from monosaccharide building blocks and afford the two glucuronoxylans in 12 and 15 % overall yield. The hexasaccharide products are valuable substrates for investigating the activity and specificity of glucuronoxylan-degrading enzymes.
Thioglycuronides: Synthesis and application in the assembly of acidic oligosaccharides
Van Den Bos, Leendert J.,Codee, Jeroen D. C.,Van Der Toorn, John C.,Boltje, Thomas J.,Van Boom, Jacques H.,Overkleeft, Herman S.,Van Der Marel, Gijsbert A.
, p. 2165 - 2168 (2007/10/03)
Partially protected thioglycuronic acids are prepared efficiently by chemo- and regioselective oxidation of the corresponding thioglycosides using the TEMPO/BAIB reagent combination. After esterification, the thioglycuronic acids proved to be useful as both donor and acceptor in sulfonium-mediated condensations toward acidic di- and trisaccharides.
Synthesis of the tetrasaccharide repeating unit of the antigen from Klebsiella type 2
Misra,Roy
, p. 103 - 111 (2007/10/03)
The disaccharide ethyl 2,4,6-tri-O-acetyl-3-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-1- thio-β-D-glucopyranoside and methyl 2,6-di-O-benzyl-3-O-(methyl 2,3,4-tri-O-benzyl-α-D-glucopyranosyluronate)-β-D-mannopyranoside have been synthesized and conden
