TY  - JOUR
A1  - Umbreen, Sumaira
A1  - Linker, Torsten
T1  - Simple Synthesis of Conformationally Fixed Glycosamine Analogues by Beckmann Rearrangement at the Carbohydrate Ring
JF  - Chemistry - a European journal
N2  - Conformationally fixed carbohydrate analogues are promising small-molecule inhibitors for hydrolases like O-GlcNAcase (OGA); however, their synthesis usually requires many steps. Herein we describe cycloadditions of dichloroketene to various glycals and subsequent Beckmann rearrangements, which offer an easy and stereoselective entry to glycosamine derivatives in good yields. The reactions are applicable for hexoses, pentoses, and disaccharides, and transformations to the corresponding imidates proceed smoothly. First biological tests reveal that such imidates indeed inhibit human OGA.
KW  - carbohydrates
KW  - cycloaddition
KW  - enzyme inhibitors
KW  - rearrangement
KW  - selective syntheses
Y1  - 2015
U6  - https://doi.org/10.1002/chem.201406546
SN  - 0947-6539
SN  - 1521-3765
VL  - 21
IS  - 20
SP  - 7340
EP  - 7344
PB  - Wiley-VCH
CY  - Weinheim
ER  -