943135-52-2Relevant academic research and scientific papers
γ-Aminoalcohol rearrangement applied to pentahydroxylated azepanes provides pyrrolidines epimeric to homoDMDP
Jagadeesh,Tran,Luo,Auberger,Désiré,Nakagawa,Kato,Zhang,Sollogoub,Blériot
, p. 3446 - 3456 (2015)
A series of pentahydroxylated pyrrolidines, displaying five contiguous stereogenic centres and epimeric to α-glucosidase inhibitor homoDMDP, have been synthesized. The key step involves a γ-aminoalcohol rearrangement applied to polyhydroxylated azepanes. These five-membered iminosugars demonstrate micromolar inhibition of glycosidases. This journal is
Access to homoglyconojirimycins via ring isomerisation of pentahydroxylated azepanes
Liu, Tao,Zhang, Yongmin,Blériot, Yves
, p. 905 - 908 (2008/02/02)
N-Benzyl pentahydroxyazepanes undergo ring isomerization during mesylation of the hydroxyl group β to the nitrogen via a neighboring nitrogen participation involving a transient aziridinium species which is trapped by chlorine. The resulting chloromethyl
