Ferric chloride: a mild and versatile reagent for the formation of 1,6-anhydro glucopyranoses |
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Authors: | Pedro O MirandaIgnacio Brouard Juan I PadrónJaime Bermejo |
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Abstract: | A novel method for the preparation of 1,6-anhydro glucopyranoses (mono- and disaccharides) utilizing anhydrous FeCl3 as Lewis acid is described. Treatment of methyl 6-O-benzyl and 6-O-p-methoxybenzyl-α/β d-glucopyranosides derivatives with FeCl3 in CH2Cl2 at room temperature and 40°C afforded 1,6-anhydro glucopyranosides in moderate to good yields, through a debenzylation and intramolecular glycosidation in one step. A plausible reaction pathway is proposed. |
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