Ferric chloride: a mild and versatile reagent for the formation of 1,6-anhydro glucopyranoses

✍ Scribed by Pedro O Miranda; Ignacio Brouard; Juan I Padrón; Jaime Bermejo

• Book ID: 104253574
• Publisher: Elsevier Science
• Year: 2003
• Tongue: French
• Weight: 322 KB
• Volume: 44
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(03)00821-9

✦ Synopsis

A novel method for the preparation of 1,6-anhydro glucopyranoses (mono-and disaccharides) utilizing anhydrous FeCl 3 as Lewis acid is described. Treatment of methyl 6-O-benzyl and 6-O-p-methoxybenzyl-a/b D-glucopyranosides derivatives with FeCl 3 in CH 2 Cl 2 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.