Tetrahedron letters

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

PO Miranda, I Brouard, JI Padrón, J Bermejo

Index: Miranda, Pedro O.; Brouard, Ignacio; Padron, Juan I.; Bermejo, Jaime Tetrahedron Letters, 2003 , vol. 44, # 20 p. 3931 - 3934

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Citation Number: 9

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-Op-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 ...