Efficient Synthesis of Azido Sugars using Fluorosulfuryl Azide Diazotransfer Reagent

22 October 2021, Version 1
This content is a preprint and has not undergone peer review at the time of posting.


Azide-containing sugars are important tools for the synthesis of biologically relevant 1,2-cis-glycosides and for bioconjugation chemistry. Previous strategies for the installation of a non-participating C2-azido functionality use harsh conditions and long reaction times. Herein, we report the synthesis of azido sugars using fluorosulfuryl azide (FSO2N3; 1) with a Cu(II) catalyst as a safe and efficient diazotransfer reagent. Common hexosamine substrates were converted to 2-azido-2-deoxy sugars in less than 5 minutes in quantitative yield. Glycosyl donors with orthogonal protecting groups were readily prepared from these azido sugars with good overall yield and a single column purification. The diazotransfer protocol was also efficiently used on other amino sugar derivatives, including aminoglycosides and substrates with amine-containing linkers. This optimized method will expand access to important non-participating C2-azido protecting groups and other azido sugar derivatives.


azido sugars
carbohydrate chemistry
chemical glycosylation

Supplementary materials

Supplementary Information - Efficient Synthesis of Azido Sugars using Fluorosulfuryl Azide Diazotransfer Reagent
Supplementary tables and figures, experimental procedures, characterization data and NMR spectra


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