The synthesis of diversely functionalized carbohydrate building
blocks is of great interest towards the generation of new carbohydrate
mimetics. Glycoaminoxy acids are recently developed glycoamino acid
analogues with both an aminoxy and a carboxyl group connected to
the sugar scaffold. These molecules could be readily used for the
synthesis of various glycoconjugates through N-oxy
amide or oxime bond, thus providing a potent tool for the design
of novel functional carbohydrate mimetics. Here, the efficient synthesis
of 2,6-functionalized pyranoid glycoaminoxy acid from commercially
available methyl glucopyranoside is reported. The subsequent assembly
of this glycoaminoxy acid building unit via N-acylation led successfully
to the novel 2,6-linked oligosaccharide mimetics.
aminoxy acids - glycoaminoxy acids - oligosaccharide mimetics - carbohydrates - oligomers
