Bamford-Stevens reaction assisted synthesis of styrene C-glycosides

Abstract

Modification of carbohydrates and their analogs is hindered due to multi-step synthetic methodologies involving selective protection and deprotection of multiple hydroxyl groups present in the molecule. A highly efficient route for the synthesis of 1-phenyl-2-(β-D-glycopyranosyl)ethenes has been developed from native sugars, which neither requires protection/deprotection of the hydroxyl groups nor use of any metal/metal ions. The key step of the developed methodology is the use of Bamford-Stevens reaction which led to the formation of the desired compounds in moderate to high yields in three steps only.

Graphical Abstract

Keywords:

• Bamford-Stevens reaction
• carbohydrates
• Glycopyranosyl ethenes
• styrene C-glycoside

Acknowledgments

BS and SK thank CSIR, New Delhi for award of Junior/Senior Research Fellowships. We are grateful to CIF-USIC, University of Delhi for providing the NMR spectral and HRMS recording facilities.

Additional information

Funding

The authors thank University of Delhi for providing financial support under DU-DST Purse Grant for the execution of the work.