860264-32-0

Upstream product

• 595559-99-2 (2R,3R,4R,5S)-6-benzylamino-1,3,4,5-O-tetrabenzyl-7-vinyl-1,2,3,4,5-heptanepentol 
• 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 
• 1354826-63-3 (3R,4R,5R,6S,7S) 7-allyl-1-benzyl-4,5,6-tris(benzyloxy)azepan-3-ol 
• 1449009-42-0 ((2S,3R,4R,5S,6S)-6-allyl-1-benzyl-3,4,5-tris(benzyloxy)piperidin-2-yl)methanol 
• 100-39-0 benzyl bromide 

Downstream Products

• 860264-56-8 7,11-anhydro-8,9,10,12-tetra-O-benzyl-7-N-benzyloxycarbonylamino-2-tert-butoxycarbonylamino-2,3,4,5,67-hexadeoxy-1-O,2-N-isopropylidene-L-threo-L-galacto-dodecitol 
• 860264-44-4 6,10-anhydro-7,8,9,11-tetra-O-benzyl-6-N-benzyloxycarbonylamino-2-tert-butoxycarbonylamino-2,3,4,5,6-pentadeoxy-1-O,2-N-isopropylidene-L-threo-L-galacto-undecitol 
• 860264-35-3 (2S,3S,4R,5R,6S)-N-benzyloxycarbonyl-6-benzyloxymethyl-3,4,5-tribenzyloxy-2-(2-propenyl)piperidine 

Relevant academic research and scientific papers

Site-Selective Debenzylation of C-Allyl Iminosugars Enables Their Stereocontroled Structure Diversification at the C-2 Position

A C-2 regioselective debenzylative cycloetherification/reductive elimination sequence applied to perbenzylated C-allyl iminosugars is described. This NIS/TMSOTf-triggered deprotection was successfully applied to five-, six-, and seven-membered C-allyl iminosugars including 1,2 cis and 1,2 trans stereoisomers. It allows rapid introduction of structural diversity at the key C-2 position in a stereoselective manner exploiting the anchimeric assistance of the intracyclic N-benzyl group, giving access to the 2-acetamido and 2-fluoro d-gluco configured C-allyl iminosugars and to the epimeric d-manno derivative.

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