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Organocatalyzed preparation of 1,4,5-trisubstituted-glycosyl-1,2,3-triazole derivatives

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Abstract

Organocatalytic coupling of glycosyl azides with enolates of active ketones and esters through azide-enolate [3 + 2] cycloaddition in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) furnished 1,4,5-trisubstituted-glycosyl-1,2,3-triazole derivatives in excellent yield. The reaction condition is simple and can be scaled-up.

Coupling of glycosyl azides with active ketones through azide-enolate [3 + 2] cycloaddition in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) furnished 1,4,5-trisubstituted-glycosyl-1,2,3-triazole derivatives in excellent yield.

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Acknowledgements

M.K. and I.B. thank CSIR, New Delhi for providing senior research fellowships. This work was supported by SERB, New Delhi (Project No. EMR/2015/000282) (AKM).

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  1. Division of Molecular Medicine, Bose Institute, P-1/12, C. I. T. Scheme VII M, Kolkata, 700054, India

    Monalisa Kundu, Ishani Bhaumik & Anup Kumar Misra

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  1. Monalisa Kundu
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Correspondence to Anup Kumar Misra.

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Kundu, M., Bhaumik, I. & Misra, A.K. Organocatalyzed preparation of 1,4,5-trisubstituted-glycosyl-1,2,3-triazole derivatives. Glycoconj J 36, 439–450 (2019). https://doi.org/10.1007/s10719-019-09883-1

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