595559-99-2

Upstream product

• 166111-63-3 N-benzyl-2,3,4,6-tetra-O-benzyl-D-glucopyranosylamine 
• 1730-25-2 allylmagnesium bromide 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 622-30-0 N-benzyl hydroxylalmine 
• 444911-50-6 1-(N-benzylhydroxylamino)-2,3,4,6-O-tetrabenzyl-1-deoxy-β-D-glucose 
• 100-46-9 benzylamine 

Downstream Products

• 860264-32-0 (2S,3S,4R,5R,6S)-N-benzyl-3,4,5-tribenzyloxy-6-benzyloxymethyl-2-(2-propenyl)piperidine 
• 595560-11-5 1-C-allyl-N-benzyl-2,3,4,6-tetra-O-benzyl-1,5-dideoxy-1,5-imino-L-iditol 
• 292062-93-2 (2R,3R,4R,5S,6R)-N-benzyl-3,4,5-tris(benzyloxy)-2-benzyloxymethyl-6-(prop-2-enyl)piperidine 

Relevant academic research and scientific papers

Synthesis of glycosylamines and glyconamides using molecular iodine

We describe herein the synthesis of glyconamides and glycosylamines usingmolecular iodine on benzylated carbohydrates. During the improvement and the optimization of the direct oxidative amidation reaction,we also discovered the possibility to form glycosylamines with excellent yields and short reaction times in comparison with the previously reported procedures. Advantages of these methods are the operational simplicity, elimination of use of complicated reagents and procedures, and generality of the reactions. Our methodology is an excellent access to precursors of N-alkyliminosugars and imino-C-glycosides.

A convenient synthesis of iminosugar-C-glycosides via organometallic addition to N-benzyl-N-glycosylhydroxylamines

N-Benzyl-N-glycosylhydroxylamines were prepared in very good yield via condensation of furanoses and pyranoses with N-benzylhydroxylamine at 110°C for 30 min under solvent-free conditions. These anomeric sugar-hydroxylamines exist in equilibrium with the

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.