Crystal structure of 6-azido-6-deoxy-1,2-O-isopropylidene-a-D-glucofuranose

Short syntheses to high Fsp³ index natural-product analogues such as imino­sugars are of paramount importance in the investigation of their biological activities and reducing the use of protecting groups is an advantageous synthetic strategy. An iso­propyl­idene group was employed towards the synthesis of seven-membered ring imino­sugars and the title compound, C₉H₁₅N₃O₅, was crystallized as an inter­mediate, in which the THF ring is twisted and the dioxolane ring adopts an envelope conformation: the dihedral angle between the rings is 67.50 (13)°. In the crystal, the hydroxyl groups participate in O—H...(O,O) and O—H...N hydrogen-bonding inter­actions, which generate chains of mol­ecules propagating parallel to the a-axis direction. There is a notable non-classical C—H...O hydrogen bond, which cross-links the [100] chains into (001) sheets.