Selective Cross‐Metathesis of C‐Allyl‐Glycosides

Abstract

The efficient and selective cross‐metathesis (CM) of both the α‐ and β‐anomers of C‐allyl‐glucose and N‐acetyl‐C‐allyl‐glucosamine with electron‐deficient olefins is reported. The applicability of our CM approach in the synthesis of glycoside‐conjugates is illustrated by the CM of α‐C‐allyl‐glycosamine 2 with uridinyl vinylphosphonate 22, to produce UDP‐GlcNAc analog 23.

Keywords:

• Synthesis
• Cross‐metathesis
• C‐glycosides
• UDP‐GlcNAc
• Inhibitor

Additional information

Notes on contributors

Jacques H. van Boom

With deep sadness the authors inform the reader that our colleague, Jacques H. van Boom, died on July 31, 2004 at the age of 67.