An efficient synthesis of alpha(2,9) trisialic acid has been achieved via one-pot glycosylation and polymer-assisted deprotection. The synthesis involves chemo- and regioselective alpha-sialylation of ethylthiosialoside with the S-benzoxazolyl (S-Box) sialyl donor. Use of a prelinker to link an activated ester and a vinyl ether via a carbon chain enables polymer-assisted deprotection of the protected trisialic acids.
In this paper, we describe an effective method for the elongation of a GlcNα(1,4)GlcAβ(1,4) sequence using a GlcNTrocα(1,4)GlcA disaccharide unit and the synthesis of the N- and/or O-sulfated GlcNα(1,4)GlcAβ(1,4) oligosaccharides. N-Troc protection of GlcNα(1,4)GlcA units was effective for the synthesis of the GlcNα(1,4)GlcAβ(1,4) oligosaccharides in comparison with the azido substituent. The GlcNα(1,4)GlcAβ(1,4) dodecasaccharide was successfully prepared by the direct β-selective glycosidation of glucuronate in the GlcNα(1,4)GlcAβ(1,4)GlcNα(1,4)GlcAβ(1,4) tetrasaccharide. In addition, the synthesis of the N- and/or O-sulfated GlcNα(1,4)GlcAβ(1,4) oligosaccharides was accomplished by fluorous-assisted deprotection and sulfation. The fluorous-assisted synthetic technology applied to the highly polar sulfated oligosaccharide permits it to be more easily separated from the highly polar reagents, such as SO(3)·NEt(3).
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.