497931-28-9

Upstream product

• 28920-43-6 (fluorenylmethoxy)carbonyl chloride 
• 950599-08-3 (2R,3S,4R,5R,6R)-2-allyl-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)piperidine 
• 292062-92-1 (3R,4R,5S,6R)-6-[N-benzyl-N-(fluoren-9-ylmethoxycarbonyl)amino]-1,3,4,5-tetrakis(benzyloxy)non-8-en-2-one 
• 1054633-26-9 (3S,4R,5S,6R)-6-Benzylamino-1,3,4,5-tetrakis-benzyloxy-non-8-en-2-one 
• 292062-93-2 (2R,3R,4R,5S,6R)-N-benzyl-3,4,5-tris(benzyloxy)-2-benzyloxymethyl-6-(prop-2-enyl)piperidine 
• 166111-63-3 N-benzyl-2,3,4,6-tetra-O-benzyl-D-glucopyranosylamine 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 

Relevant academic research and scientific papers

Synthesis of nojirimycin C-glycosides

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.