Nojirimycin α-C-glycosides, which have 1-α-allyl-1-deoxy-N-benzyl-2,3,4,6-tetra-O-benzylnojirimycin (9) as a key intermediate for further derivatisation, have been synthesized from commercially available 2,3,4,6-tetra-O-benzyl-D-glucopyranose (3) through a highly stereoselective procedure which involves treatment of 3 with benzylamine, reaction of the obtained glucosylamine 4 with allylmagnesium bromide and cyclization of the elongated open-chain aminosugar 5 by Fmoc-protection, oxidation of the free hydroxy group, and intramolecular reductive-amination, affording 9 in 59% overall yield. The efficient manipulation of the allylic appendage of 9 has required N-debenzylation and Fmoc-protection of the ring-nitrogen.
Cipolla, L., Palma, A., LA FERLA, B., Nicotra, F. (2002). Synthesis of Nojirimycin C-glycosides. JOURNAL OF THE CHEMICAL SOCIETY. PERKIN TRANSACTIONS. 1, 2(19), 2161-2165 [10.1039/B206623H].
Synthesis of Nojirimycin C-glycosides
CIPOLLA, LAURA FRANCESCA;LA FERLA, BARBARA;NICOTRA, FRANCESCO
2002
Abstract
Nojirimycin α-C-glycosides, which have 1-α-allyl-1-deoxy-N-benzyl-2,3,4,6-tetra-O-benzylnojirimycin (9) as a key intermediate for further derivatisation, have been synthesized from commercially available 2,3,4,6-tetra-O-benzyl-D-glucopyranose (3) through a highly stereoselective procedure which involves treatment of 3 with benzylamine, reaction of the obtained glucosylamine 4 with allylmagnesium bromide and cyclization of the elongated open-chain aminosugar 5 by Fmoc-protection, oxidation of the free hydroxy group, and intramolecular reductive-amination, affording 9 in 59% overall yield. The efficient manipulation of the allylic appendage of 9 has required N-debenzylation and Fmoc-protection of the ring-nitrogen.
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