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Abstract
The reductive cleavage of benzyl 2-benzyloxycarbonylamino-2-deoxy-4,6-O-(2-methoxybenzylidene)-α-D-glucopyranoside 2 with LiAlH4-AlCl3 gave the corresponding 4-O-(2-methoxybenzyl) ether along with the 6-O-ether as expected. When, however, the 3-hydroxyl group was substituted, acetal cleavage was not the main reaction path. With a 3-O-allyl or a 3-O-methyl group, the unsymmetrical urea derivatives 8 resulted together with the formamido and N-methylamino derivatives 9 and 10, respectively, and no acetal cleavage was observed. Substitution at O-3 with a benzyl group allowed the formation of a small amount of 4-O-ether along with the formamido and N-methylamino derivatives with intact 2-methoxybenzylidene group.
1. Summer student 1996 from the Institut Universitaire Professionalisé Orléans, France.
2. Summer student 1995 from the Institut Universitaire Professionalisé Orléans, France.
Notes
1. Summer student 1996 from the Institut Universitaire Professionalisé Orléans, France.
2. Summer student 1995 from the Institut Universitaire Professionalisé Orléans, France.
Summer student 1996 from the Institut Universitaire Professionalisé, Orléans, France.
Summer student 1995 from the Institut Universitaire Professionalisé, Orléans, France.
It is interesting to note, however, that the treatment of isolated formamido derivative 9c with LiAlH4/ AlCl3 under analogous reaction conditions did not lead to further transformations, i.e. did not yield the N-methylamino derivative 10c.