Neoglycosylation, a single-step coupling reaction between an unprotected free-reducing sugar and an N-alkyl-N-alkoxy amine, can be used to generate analogues of bioactive compounds bearing a range of sugar attachments. As this approach requires the availability of diverse free-reducing sugar building blocks, our group’s recent focus has been on the synthetic design and optimization of various pathways leading to stereochemically varied 2-amino free-reducing sugars. Using rhodium- and copper-nitrene mediated amidoglycosylation reactions of glycals, we have prepared carbohydrate frameworks bearing a C2-N,C3-O oxazolidinone ring and incorporating a transient protecting group at the anomeric site. Next, deprotection of the 4O and 6O positions, as well as the anomeric center, produced the fully deprotected free-reducing sugars. We have subsequently demonstrated neoglycosylation with several model N-alkyl-N-alkoxyamines and are also exploring 2-amino free-reducing sugars bearing C6-azido functionality as well as N-aryl substitution on the oxazolidinone ring.

Synthesis and neoglycosylation with stereo-diverse 2-amino free-reducing sugars

253rd National Meeting (2017)

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