Synthesis of Novel Glycoconjugates Derived From Alkynyl Heterocycles through a Click Approach

Abstract

The synthesis of a series of novel 1,4-disubstituted 1,2,3-triazole compounds bearing a D-glucose derivative and an heteroaromatic system is described. Alkylation of isatin, 3-methyl-carbazole, and one tetrahydro-γ-carboline with propargyl bromide gave their N-propargyl derivatives in good yields. These compounds further reacted with acetylated D-glucose with the azide group in position 1 to give three final products and with peracetylated 6-azido-6-deoxy-α-D-methylglucoside, giving the corresponding derivative of tetrahydro-γ-carboline.

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GRAPHICAL ABSTRACT

Keywords:

• Alkynyl heterocycles
• azido sugars
• click chemistry
• 1,2,3-triazoles

ACKNOWLEDGMENTS

We gratefully acknowledge the financial support from FCT (Fundaçãopara a Ciência e Tecnologia) and FEDER for National NMR Network (Bruker Avance II 400) and REEQ/630/QUI/2005 (LC/MS instrument).