2'-Fluoromaltose: Synthesis and Properties of 4-0-(2-Deoxy-2-fluoro-α-D-Glucopyranosyl)-D-Glucopyranose, and the Crystal Structure of 2,3-Di-O-Acetyl-1,6-Anhydro-4-0-(3,4-Tri-0-Acetyl-2-Deoxy-2-Fluoro-α-Gluco-pyranosyl)-alpha-D-Glucopyranose
Shelling, J.G., David Dolphin, Wirz, P., Cobbledick, R.E., and Einstein, F.W.B.
Coupling of 3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-α-D-glucopyranosyl bromide and 3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-α-D-galactopyranosyl bromide with 2,3-di-O-acetyl-1,6-anhydro-β-D-glucose, under Koenigs-Knorr reaction conditions gave, in both instances, only the corresponding β -(1→4)-linked disaccharides. In the first case, the linkage was verified by 1H- and 19F-NMR, and by x-ray crystallography of 2,3-di-O-acetyl-1,6-anhydro-4-O-(3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-α-D-glucopyranosyl)-β-D-glucopyranose. Deprotection of this disaccharide gave 2'-deoxy-2'-fluoromaltose. Maltose and its fluorinated analog displayed similar 1H- and 13C-NMR spectra and optical rotations, indicating that these two sugars are isomorphous in soln. and suggesting that 2'-deoxy-2'-fluoromaltose might be a suitable substrate for studies of α-glycosidases.