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null (Ed.)Reported herein is a new method for a highly effective synthesis of β-glycosides from mannuronic acid donors equipped with the 3- O -picoloyl group. The stereocontrol of glycosylations was achieved by means of the H-bond-mediated aglycone delivery (HAD). The method was utilized for the synthesis of a tetrasaccharide linked via β-(1 → 3)-mannuronic linkages. We have also investigated 3,6-lactonized glycosyl donors that provided moderate to high β-manno stereoselectivity in glycosylations. A method to achieve complete α-manno stereoselectivity with mannuronic acid donors equipped with 3- O -benzoyl group is also reported.more » « less
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null (Ed.)O -Picoloyl protecting groups at remote positions can affect the stereoselectivity of glycosylation by means of the H-bond-mediated aglycone delivery (HAD) pathway. A new practical method for the stereoselective synthesis of β-glycosides of mannosamine is reported. The presence of the O -picoloyl group at the C-3 position of a mannosamine donor can provide high or complete stereocontrol. The method was also utilized for the synthesis of a biologically relevant trisaccharide related to the capsular polysaccharide of Streptococcus pneumoniae serotype 4. Also reported herein is a method to achieve complete α-manno stereoselectivity with mannosamine donors equipped with 3- O -benzoyl group.more » « less
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Abstract The main focus of this review is to describe accomplishments made in the stereoselective synthesis of
β ‐linked mannosides functionalized with carboxyls or amines/amides. These ManNAc, ManA and ManNAcA residues found in many glycoconjugates, bacterial polysaccharides, and alginates have consistently captured interest of the glycoscience community both due to synthetic challenge and therapeutic potential.
