2'-FLUOROMALTOSE: SYNTHESIS AND PROPERTIES OF 4-O-(2-DEOXY-2-FLUORO-α-D-GLUCOPYRANOSYL)-D-GLUCOPYRANOSE, AND THE CRYSTAL STRUCTURE OF 2,3-DI-O-ACETYL-1,6-ANHYDRO-4-O-(3,4-TRI-O-ACETYL-2-DEOXY-2-FLUORO-α-D-GLUCOPYRANOSYL)-β-D-GLUCOPYRANOSE

Article abstract of DOI:10.1016/0008-6215(84)85222-2

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 α-(1->4)-linked disaccharides.In the first case, the linkage was verified by 1H- and 19F-n. m. r., and by X-ray crystallographic analysis 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 analogue displayed similar 1H- and 13C-n. m. r. spectra and optical rotations, indicating that these two sugars are isomorphous in solution and suggesting that 2'-deoxy-2'-fluoromaltose might be a suitable substrate for studies of α-glycosidases.