Unique tetrameric and hexameric mannoside clusters prepared by click chemistry

• We have presented a facile synthesis of unique tetrameric and hexameric mannoside clusters.
• The synthesis was achieved by using the copper mediated Huisgen 1,3-dipolar cycloaddition, also referred to as click chemistry.
• The presented mannoside clusters are equipped with an aglycone whose length is designed to fit in the tyrosine gate.
• The unprotected mannosides were found to exhibit good water solubility, a prerequisite for biological activity.

The synthesis of novel tetrameric and hexameric mannoside clusters bearing 1,2,3-trizole linkages via Cu(I)-catalyzed azide–alkyne cycloaddition reaction (“click chemistry”) is described. An attractive feature of these multiarmed mannoside clusters as potential inhibitors of uropathogenic Escherichia coli is the use of an aglycone whose length is designed to fit in the tyrosine gate. The acetylated mannosides were deprotected and the corresponding de-O-acetylated mannosides were found to exhibit good water solubility.

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