An easy route to functionalize monosaccharaides at the 6th carbon position was studied for different functional groups. As a proof of concept for this synthetic pathway, hexoses in the pyranose form were selectively protected and synthesized as a mixture of a,� anomers of 1,2,3,4-tetra-O-acetyl-6-O-trityl-D-monosacharidesto react at the primary carbon without deprotection, as is usually required for functionalization.  Functionalization was explored using different substrates, such as mannose, glucose, galactose and �-cyclodextrin. The protected monosaccharides were reacted with several electrophiles to introduce various functional groups, such as ester, ether, silyl ether and 1,6-O-glycosidic bonds.  Several of the functionalized saccharaides are being applied to the synthesis of glycopolymers.

Functionalization of monosaccharides with electrophiles

245th National Meeting (2013)

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