L. Cipolla, B. L. Ferla, F. Peri
2000
Citations
0
Influential Citations
27
Citations
Journal
Chemical Communications
Abstract
Reaction with allylmagnesium bromide of N,2,3,4,6-pentabenzyl-D-glucopyranosylamine 2, obtained from tetrabenzylglucose and benzylamine, afforded stereoselectively the open chain amino alcohol 3, which was converted into the C-glycoside of nojirimycin 6 by full protection of the amino function by Fmoc, oxidation of the free hydroxy group, hydrolysis of the Fmoc group and final intramolecular reductive amination with NaBH(OAc)3; compound 6 was also converted into methyl ketone 7, by manipulation of the allylic appendage.