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InCl₃–CH₃CN–H₂O: an efficient catalyst-solvent combination for the synthesis of Perlin aldehydes and related compounds. Application in the synthesis of unnatural l-azasugars

Author:
Nagaraj, Paramathevar, Ganesan, Muthupandian, Ramesh, Namakkal G.
Source:
Tetrahedron 2011 v.67 no.4 pp. 769-776
ISSN:
0040-4020
Subject:
aldehydes, chemical reactions, chemical structure, galactosidases, glucosidases
Abstract:
InCl₃–CH₃CN–H₂O has been found to be an efficient catalyst-solvent combination for the synthesis of Perlin aldehydes and related compounds. While acetylated glycals afforded the Perlin aldehydes directly with InCl₃ and water, benzylated glycals on the other hand provided the hemiacetals under identical condition. The methodology reports a non-mercurial approach to Perlin aldehydes. Noteworthy is that this reaction is more facile as well as highly selective with glycals possessing a hydroxyl as a leaving group than with a benzyloxy group. Extension of this reaction to 2-C-hydroxymethyl glycals resulted in the formation of the corresponding hemiacetals, which were further transformed in to unsaturated azasugars with an exo-methylene group at C-2 position. Glycosidase inhibition studies reveal that these compounds display selectivity in inhibiting glucosidases rather than galactosidases.
Agid:
1093384