A Convenient Synthesis of Type IV Glycosyl Donors from Type I Disaccharides

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Abstract
The synthesis of 4,6-di-O-acetyl-3-O-(tetra-O-acetyl-ß-D-galactopyranosyl)-2-deoxy-2-phthalimido-α,ß-D-galactopyranosyl chloride 1 4 and its 6-O -benzyl derivative 1 2 was achieved in a 5-step sequence starting from the readily available type I disaccharide derivative 3. The key step in the synthesis involved the preparation of trifluoromethanesulfonate (triflate) derivatives 7 and 9 and their subsequent SN2 displacement by acetate ion for conversion of 2-deoxy-2-phthalimido-ß-D-glucopyranosyl moiety to the corresponding galacto configuration.