Premium
Synthesis of Imino Sugar Scaffolds for the Generation of Glycosidase Inhibitor Libraries
Author(s) -
La Ferla Barbara,
Bugada Piergiuliano,
Cipolla Laura,
Peri Francesco,
Nicotra Francesco
Publication year - 2004
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200300805
Subject(s) - chemistry , stereocenter , amine gas treating , primary (astronomy) , aldehyde , stereochemistry , ring (chemistry) , derivatization , nitrogen atom , sugar , amino acid , organic chemistry , enantioselective synthesis , biochemistry , catalysis , physics , high performance liquid chromatography , astronomy
We have synthesized imino sugar scaffolds bearing two points of diversity — the stereocenters located in α positions relative to the nitrogen atom — and three points of orthogonal derivatization — a carboxylic function, the primary hydroxy group, and the ring nitrogen atom. The key steps in the synthetic approach are the chain elongation of aldehyde 5 with the formation of an α,β‐unsaturated ester, the Michael addition of an amine, and the final cyclization. This strategy leads to the preparation of different N ‐substituted imino sugar analogues having both α and β structures and of both D and L stereochemistry. Different derivatives have been prepared from the scaffolds we obtained. The carboxymethyl group was coupled to the amino function of different amino acids to afford compounds 30 − 34 , while the selectively accessible primary hydroxy group has been substituted with an azido group to afford compounds 24 − 26 . (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)