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.

Cipolla, L., LA FERLA, B., Peri, F., & Nicotra, F. (2000). A new procedure for the synthesis of C-glycosides of nojirimycin. CHEMICAL COMMUNICATIONS(14), 1289-1290 [10.1039/b003877f].

A new procedure for the synthesis of C-glycosides of nojirimycin

CIPOLLA, LAURA FRANCESCA;LA FERLA, BARBARA;PERI, FRANCESCO;NICOTRA, FRANCESCO
2000

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.
Articolo in rivista - Articolo scientifico
Scientifica
Iminosugars, Nojirimycin
English
Cipolla, L., LA FERLA, B., Peri, F., & Nicotra, F. (2000). A new procedure for the synthesis of C-glycosides of nojirimycin. CHEMICAL COMMUNICATIONS(14), 1289-1290 [10.1039/b003877f].
Cipolla, L; LA FERLA, B; Peri, F; Nicotra, F
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/10281/16670
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