Chen, Jian; Hansen, Thomas; Zhang, Qing-Ju; Liu, De-Yong; Sun, Yao; Yan, Hao; Codee, Jeroen D. C.; Schmidt, Richard R.; Sun, Jian-Song published the artcile< 1-Picolinyl-5-azido Thiosialosides: Versatile Donors for the Stereoselective Construction of Sialyl Linkages>, HPLC of Formula: 4064-06-6, the main research area is glycan sialooligosaccharide preparation sialylation picolinyl azido protected thiosialoside; directing groups; glycan antennae; glycosylation; sialoside; stereoselective sialylation.
With the picolinyl (Pic) group as a C-1 located directing group and N3 as versatile precursor for C5-NH2, a novel 1-Pic-5-N3 thiosialyl donor was designed and synthesized, based on which a new sialylation protocol was established. In comparison to conventional sialylation methods, the new protocol exhibited obvious advantages, including excellent α-stereoselectivity in the absence of a solvent effect, broad substrate scope encompassing the challenging sialyl 8- and 9-hydroxy groups of sialic acid acceptors, flexibility in sialoside derivative synthesis, high temperature tolerance and easy scalability. In particular, the applicability to the synthesis of complex and bioactive N-glycan antennae when combined with the MPEP glycosylation protocol via the “”latent-active”” strategy has been shown. Mechanistically, the excellent α-stereoselectivity of the novel sialylation protocol could be attributed to the dramatic electron-withdrawing effect of the protonated Pic groups, which was supported by control reactions and DFT calculations
Angewandte Chemie, International Edition published new progress about Diastereoselective synthesis. 4064-06-6 belongs to class alcohols-buliding-blocks, and the molecular formula is C12H20O6, HPLC of Formula: 4064-06-6.
Referemce:
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