Stereoselective synthesis of α-glycosyl azides by ring-opening of 1,6-anhydrosugars with trimethylsilyl azide

• Expedient and stereoselective synthesis of α-glycosyl azides.
• In some cases, α-only selectivity and generally high yields achieved.
• Applicable to substrates with various protecting groups and oligosaccharides.
• The synthesized α-glycosyl azides is of great utility and potential.

We describe here an expedient and highly stereoselective procedure for the synthesis of α-glycosyl azides. Treatment of 1,6-anhydrosugars with trimethylsilyl azide in the presence of trimethylsilyl triflate led to the formation of α-glycosyl azides. All the reactions were highly stereoselective and afforded the α-glycosyl azides in good to excellent yields.

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