Regioselective alkylation of benzyl?-d-lactoside and its derivatives by stannylation

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The preparation of benzyl 2,3,6,2′,6′-penta-O-benzyl-β-d-lactoside, which is a key intermediate for chemical synthesis of oligosaccharide components of glycosphingolipids, was achieved by an improved method. The 3′-O-p-methoxybenzyl and 3′-O-methyl derivatives were prepared from benzyl 2,3,6,2′,6′-penta-O-benzyl-β-d-lactoside through stannylation. By using benzyl β-d-lactoside as starting material, benzyl 3′-O-methyl-, 3′-O-benzyl- and 3′-O-p-methoxybenzyl-β-d-lactoside were regioselectively synthesized using the same procedure.

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