Crystal structure of 6-azido-6-de­oxy-1,2-O-iso­propyl­idene-α-d-gluco­furan­ose

Short syntheses to high Fsp (3) 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, C(9)H(15)N(3)O(5), 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.