Synthesis of Divalent 2,2 '-Linked Mannose Derivatives by Homodimerization

Several studies have implicated (1 -> 2)-linked mannans as biologically relevant compounds. Recently, there has been a growing interest in the synthesis of multivalent carbohydrate assemblies due to their ability to target multiple receptors simultaneously. In the present work, a protective group strategy, based oil the methodology originally developed by Crich, has been utilized for the homodimerization of olefinic carbohydrates, allowing a highly diastereoselective synthesis of some divalent structures. Furthermore, it is shown that divalent donors tray undergo coupling reactions without losses ill stereoselectivity or efficiency, The strategies described may potentially be applied to the synthesis of diverse neoglycoconjugates and of oligosaccharides.