A new approach to the synthesis of 1, 6‐anhydro‐2‐azido‐2‐deoxy‐β‐D‐glucopyranose derivatives

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Abstract
1, 6‐Anhydro‐β‐D‐mannopyranose was converted in three steps into 1, 6‐anhydro‐3‐0‐(4‐methoxybenzoyl)‐4‐0‐allyl‐β‐D‐mannopyranose in high overall yield. Treatment of the latter with trifluoromethanesulphonic anhydride, followed by direct displacement at 20°c of the triflate ester with lithium azide afforded almost quantitatively 1, 6‐anhydro‐2‐azido‐2‐deoxy‐3‐0‐(4‐methoxybenzoyl)‐4‐0‐allyl‐β‐D‐glucopyranose.