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Glycosylations have been used repeatedly as the key reaction in the synthesis of oligosaccharides and polysaccharides, therefore both of e‹ciency and stereoselectivity of the glycosylations are important. There has been reported the construction of 1,2-cis glycoside found in various bioactive glycoconjugate glycans from eukaryotes as well as prokaryotes, although a few for the deˆnite methodologies to construct stereoselectively. Approaching from both e‹ciency and stereoselectivity of the reactions, we developed various highly e‹cient and stereocontrolled O-glycosylation methodologies for the construction of 1,2-cis glycosides. We also showed that their 1,2-cis glycosylation methodologies have been applied to the stereoselective synthesis of various bacterial glycoconjugate glycans. A. Introduction 1,2-Cis O-glycosides are important constituents of various biologically active natural products and glycoconjugates (1,2). a-Glycosides of D-glucose (Glc), L-fucose (Fuc), and a b-glycoside of D-mannose (Man) are major constituents of asparagine-linked (N-linked) glycoproteins and an a-glycoside of N-acetyl-D-galactosamine (GalNAc) constitutes the core structure of serine/threonine-linked (O-linked) glycoproteins (Fig. 1). In the bacterial glycoconjugates and polysaccharides, various 1,2-cis linkages, such as b-glycoside of D-arabinofuranoside and aglycosides of D-GalNAc and L-rhamnose, are also included. Although 1,2-trans-isomers have been obtained stereoselectively through the eŠect on neighboring group participation of the C-2 substituent such as acyl group, there has been reported a few deˆnite methodologies to construct 1,2-cis isomers stereoselectively. Although key

trends in glycoscience and glycotechnology

Development of highly efficient and stereocontrolled &lt;i&gt;O&lt;/i&gt;-glycosylation methodologies and its application to the construction of bacterial glycans