AI Article Synopsis
- - The study details the total synthesis of a specific hexasaccharide that is part of the O-antigen from Shigella flexneri serotype 1d, which has a complex structure involving multiple sugar units.
- - The synthesis was accomplished using a linear strategy that included sequential glycosylations of protected monosaccharide derivatives, which were modified from commercially available sugars.
- - A novel method using H2SO4-silica to activate thioglycosides was found to be more effective than traditional reagents, improving the efficiency of the stereoselective glycosylation process.
Article Abstract
Total synthesis of the hexasaccharide repeating unit of the O-antigen from Shigella flexneri serotype 1d (I: 7,8), α-D-Glcp-(1→3)-α-L-Rhap-(1→2)-α-L-Rhap-(1→3)-α-L-Rhap-(1→3)-[α-D-Glcp-(1→4)]-β-D-GlcpNAc, is reported by following a linear strategy. The target hexasaccharide was synthesized by sequential glycosylations of suitably protected monosaccharide derivatives prepared from commercially available monosaccharides through rational protecting group manipulations. Stereoselective glycosylations were accomplished by the activation of thioglycoside using N-iodosuccinimide and H2SO4-silica. The use of H2SO4-silica in place of traditional promoters like TfOH or TMSOTf was proved to be a better option for the NIS-mediated thioglycoside activation.
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| http://dx.doi.org/10.1016/j.carres.2016.03.012 | DOI Listing |
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