Author : Ibrahim Mohammed, Adnan
journal of kerbala university,
2010, Volume 6, Issue 3, Pages 42-48
Acetylation of D-glucose using acetic anhydride and sodium acetate gave 1,2,3,4,6-penta-O-acetyl-β-D-glucopyranose (1). Reaction of (1) with hydrobromic acid in glacial acetic acid gave 2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl bromide (2). SN2 reaction of (2) with sodium azide in DMF yielded 2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl azide (3). Glycosidation of (1) in the presence of tin (IV) chloride afforded 2-Propynyl (2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside) (4). All of prepared compounds have been characterized by TLC, FT-IR, 1H NMR, 13C NMR and two dimensional NMR (COSY and HSQC) in order two assign the exact protons and carbons of the glupyranosyl ring.