The use of tri-O-acetyl-d-glucal and -d-galactal in the synthesis of ω-aminoalkyl 2-deoxy- and 2,3-dideoxy-d-hexopyranosides

We report a simple, efficient, and mild method for the synthesis of ω-aminoalkyl 2-deoxy-d-arabino/lyxo-hexopyranoside and 2,3-dideoxy-α-d-erythro-hexopyranoside. The total synthesis is accomplished in two sequential reactions. The first step consists of an addition reaction of N-(ω-hydroxyalkyl)phthalimide and N-(ω-hydroxyalkyl)succinimide to peracetylated d-glycals, which is promoted by triphenylphosphine hydrobromide or borontrifluoride/diethyl etherate. The second step involves reacting the appropriate glycoside with methylamine.