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

AuthorsMiranda, Pedro O. ; Brouard, Ignacio ; Padrón, Juan I. ; Bermejo, Jaime
KeywordsFerric chloride
1,6-anhydro glucopyranoses
Lewis acid
Issue Date12-May-2003
PublisherElsevier BV
CitationTetrahedron Letters 44(20): 3931-3934 (2003)
AbstractA 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.
Publisher version (URL)https://doi.org/10.1016/S0040-4039(03)00821-9
Identifiersdoi: 10.1016/S0040-4039(03)00821-9
issn: 0040-4039
Appears in Collections:(IPNA) Artículos
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