166111-63-3

Upstream product

• 59531-24-7 2,3,4,6-tetra-O-benzyl-D-glucopyranoside 
• 100-46-9 benzylamine 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 

Downstream Products

• 292165-63-0 (1R)-1-C-allyl-2,3,4,6-tetra-O-benzyl-1-benzylamino-1-deoxy-D-glucitol 
• 595559-99-2 (2R,3R,4R,5S)-6-benzylamino-1,3,4,5-O-tetrabenzyl-7-vinyl-1,2,3,4,5-heptanepentol 
• 595560-11-5 1-C-allyl-N-benzyl-2,3,4,6-tetra-O-benzyl-1,5-dideoxy-1,5-imino-L-iditol 
• 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 
• 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 
• 1054633-26-9 (3S,4R,5S,6R)-6-Benzylamino-1,3,4,5-tetrakis-benzyloxy-non-8-en-2-one 
• 950599-08-3 (2R,3S,4R,5R,6R)-2-allyl-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)piperidine 
• 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

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.

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.

Synthesis of new β-1-C-alkylated imino-l-iditols: A comparative study of their activity as β-glucocerebrosidase inhibitors

A short synthesis of new β-1-C-alkyl-1,5-dideoxy-1,5-imino-l-iditols by means of the diastereoselective addition of Grignard reagents onto a glucopyranosylamine is described. These compounds were evaluated as β-glucocerebrosidase inhibitors and their activity was compared with that of related iminosugar derivatives in the d-gluco and d-xylo series. The results allowed us to conclude on the influence of the hydroxymethyl moiety and of the piperidine-ring conformation on the inhibitory activity.

Access to ring-expanded analogues of 2-amino sugars

Ring-expanded 2-Nacetylamino sugar analogs of D-glucose, D-galactose, and D-mannose have been prepared by a new synthetic route. Aspects of the highly substituted a-amio aldehyde Intermediates made them central to the approach. First, they were accessed v

Synthesis and biological evaluation of a small library of nojirimycin-derived bicyclic iminosugars

Novel nojirimycin-derived bicyclic structures, containing cyclic carbamate, urea and guanidine moieties have been synthesised starting from suitably protected α-C-vinylnojirimycin and α-C-allylnojirimycin, respectively, and their biological activity against different glycosidases and as antibacterial agents tested.

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.

Synthesis of azasugars by Grignard reaction on glycosylamines

Pyrrolidines 5a-b, and piperidines 10a,b and 15, were synthesised by Grignard reaction on a glycosylamine, easily obtained from the parent sugar and a primary amine, followed by cyclization with triflic anhydride.