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Access to α‐glycosyl azides in modest to high diastereoselectivity by way of TMSN3 ring‐opening of 1,6‐anhydro sugars mediated by TMSOTf is reported. The reaction tolerates a wide variety of functional groups including alcohol, alkyne, azide and ester groups. The efficient synthesis of a pseudopentasaccharide in five steps from commercially available levoglucosan by way of a “click‐click” approach...
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