Carbohydrate Research p. 241 - 260 (1984)
Update date:2022-08-04
Topics:
Shelling, Judith G.
Dolphin, David
Wirz, Peter
Cobbledick, Roger E.
Einstein, Frederick 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 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.
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