292062-93-2

Upstream product

• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 595559-99-2 (2R,3R,4R,5S)-6-benzylamino-1,3,4,5-O-tetrabenzyl-7-vinyl-1,2,3,4,5-heptanepentol 
• 100-46-9 benzylamine 
• 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 
• 166111-63-3 N-benzyl-2,3,4,6-tetra-O-benzyl-D-glucopyranosylamine 
• 1054633-26-9 (3S,4R,5S,6R)-6-Benzylamino-1,3,4,5-tetrakis-benzyloxy-non-8-en-2-one 

Downstream Products

• 950599-08-3 (2R,3S,4R,5R,6R)-2-allyl-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)piperidine 
• 497931-28-9 (2R,3R,4R,5S,6R)-3,4,5-tris(benzyloxy)-2-benzyloxymethyl-N-(fluoren-9-ylmethoxycarbonyl)-6-(prop-2-enyl)piperidine 
• 1054653-75-6 (2R,3R,4R,5S,6R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-(2-oxo-ethyl)-piperidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester 

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.

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

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.