Xie Juan, Ménand Mickaël, Valéry Jean-Marc
Synthèse, Structure et Fonction des Molécules Bioactives, CNRS UMR 7613, Equipe Chimie des Glucides, Université Pierre et Marie Curie, 4 Place Jussieu, F-75005 Paris, France.
Carbohydr Res. 2005 Feb 28;340(3):481-7. doi: 10.1016/j.carres.2004.12.001.
Boron trichloride has been found to promote selective deprotection of 1,2- or 1,3-cis oriented secondary benzyl ethers of per-benzylated C-glycosyl derivatives. The reactivity towards BCl(3) follows the order: C-4>or=C-2>C-6>C-3 for C-glucopyranosyl derivatives and C-3>or=C-4>C-6>C-2 for C-galactopyranosyl derivatives. Preparatively useful selective debenzylation at secondary positions was possible after careful control of reaction conditions.
