Regioselective debenzylation of C-glycosyl compounds by boron trichloride.
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.
Xie
Juan
J
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. joanne.xie@ppsm.ens-cachan.fr
Ménand
Mickaël
M
Valéry
Jean-Marc
JM
D001593:Benzyl Compounds / Q000737:chemistry*; D001880:Boranes / Q000737:chemistry*; D002712:Chlorides / Q000737:chemistry*; D004987:Ethers / Q000737:chemistry; D006601:Hexoses / Q000737:chemistry*
D001593:Benzyl Compounds; D001880:Boranes; D002712:Chlorides; D004987:Ethers; D006601:Hexoses; C092267:boron trichloride