Reductive openings of benzylidene acetals. Kinetic studies of borane and alane activation by Lewis acids.
The reaction kinetics for a number of reductive openings of methyl 2,3-di-O-benzyl-4,6-O-benzylidene-alpha-d-glucopyranoside have been investigated. Openings to give free HO-6 (using BH(3).THF-AlCl(3)-THF or LiAlH(4)-AlCl(3)-Et(2)O) follow first order kinetics, while reactions yielding free HO-4 (using BH(3).NMe(3)-AlCl(3)-THF or BH(3).NMe(3)-BF(3).OEt(2)-THF) follow higher order kinetics. The add