147126-57-6

Upstream product

• 111-87-5 octanol 
• 7512-17-6 N-Acetyl-D-glucosamine 
• 1040191-33-0 N'-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-p-toluenesulfono-hydrazide 

Downstream Products

• 215302-00-4 N-((4aR,6S,7R,8R,8aS)-8-Hydroxy-6-octyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-acetamide 
• 368870-54-6 octyl 2-acetamido-2-deoxy-6-O-trityl-α-D-glucopyranoside 
• 1033561-27-1 n-octyl 2-acetamido-2-deoxy-4,6-O-benzylidene-α-D-glycopyranoside 
• 869338-87-4 octyl 2-acetamido-2-deoxy-4,6-O-(4-methoxybenzylidene)-α-D-glucopyranoside 
• 869338-88-5 Acetic acid (2R,4aR,6S,7R,8R,8aS)-7-acetylamino-2-(4-methoxy-phenyl)-6-octyloxy-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester 
• 869338-81-8 octyl 2-acetamido-3-O-acetyl-2-deoxy-4-O-(4-methoxybenzyl)-α-D-glucopyranoside 
• 368870-56-8 octyl 2-acetamido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranoside 
• 368870-55-7 octyl 2-acetamido-3,4-di-O-benzyl-2-deoxy-6-O-trityl-α-D-glucopyranoside 
• 215302-36-6 octyl O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->3)-O-[(2,3,4,6-tetra-O-benzoyl)-β-D-galactopyranosyl-(1->6)]-2-acetamido-2-deoxy-α-D-glucopyranoside 
• 215302-02-6 N-[(2S,3R,4R,5S,6R)-5-Hydroxy-6-hydroxymethyl-2-octyloxy-4-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide 
• 215302-01-5 N-[(4aR,6S,7R,8R,8aS)-6-Octyloxy-2-phenyl-8-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide 
• 215302-21-9 N-[(2S,3R,4R,5S,6R)-6-((S)-2,2-Dimethyl-[1,3]dioxolan-4-ylmethoxymethyl)-5-hydroxy-2-octyloxy-4-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide 
• 215302-25-3 N-[(2S,3R,4R,5S,6R)-5-((S)-2,2-Dimethyl-[1,3]dioxolan-4-ylmethoxy)-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxymethyl)-2-octyloxy-4-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide 

Relevant academic research and scientific papers

Central neural tumor destruction by controlled release of a synthetic glycoside dispersed in a biodegradable polymeric matrix

An octyl N-acetylglucosaminide derivative with a pentaerythritol chain at position 6 has been synthesized and evaluated as an inhibitor of neural tumor growth. The glycoside inhibited the growth of a neuroectodermic tumor implanted in rats and, when loade

A new synthesis of O-glycosides from totally O-unprotected glycosyl donors

O-Glycosidation of the totally O-unprotected aldoses (D-glucose, D-galactose and D-mannose) and D-fructose in THF or 1,4-dioxane using anhydrous FeCl3 as promoter afforded either aldofuranosides 1, 3, 4 in good overall yields or exclusively β-D-fructopyranosides 7. Conversely α-D-aldopyranosides 2, 5 and 6 were obtained respectively from D-glucose, D-mannose and N-acetyl-D-glucosamine when the reactions were performed in the presence of BF3.OEt2 under ultrasonication.

Straightforward glycosylation of alcohols and amino acids mediated by ionic liquid

Green glycosylation of functionalized alcohols and α-amino acids, using an ionic liquid as a recyclable solvent, was performed in one step directly from the unprotected monosaccharide under scandium triflate or ferric chloride catalysis. Pure α- and β-glycosides could be obtained after specific enzymatic hydrolysis.

Ionic liquid promoted atom economic glycosylation under Lewis acid catalysis

Straightforward glycosylation of various alcohols with unprotected and non-activated monosaccharides were performed under scandium triflate catalysis. Rate and yield of glycosylation were highly improved when using 1-butyl-3-methylimidazolium trifluoromethanesulfonate as a green solvent. This ionic liquid was allowed to be recycled at least three times without loss of activity. The possibility of drastically reducing the amounts of catalyst (down to 1 mol%) and aglycone (down to 1 equiv) when performing the reaction in ionic liquid opens new perspectives in O-glycosylation, as a direct coupling between an aglycone and free sugars.

Protecting group free glycosidations using p-toluenesulfonohydrazide donors

(Figure Presented) N-Glycopyranosylsulfonohydrazides are introduced as glycosyl donors for protecting group free synthesis of O-glycosides, glycosyl azides, and oxazolines. Mono- and disaccharides containing a reducing terminal N-acelylglucosamine residue were condensed with p-toluenesulfonylhydrazide to give the desired β-D-pyranose donors. These donors can be activated with NBS and then glycosidated with the desired alcohol or transformed to the oxazoline or glycosyl azide.

Design and synthesis of glycoside inhibitors of glioma and melanoma growth

An N-acetylglucosaminide derivative with a pentaerythritol substituent at position C-6 was previously synthesized and shown to inhibit neural tumor growth. Now, we report the preparation of a series of new synthetic compounds introducing systematic change

Novel disaccharide inhibitors of human glioma cell division

Several α-L-Fuc-(1→3)-α-D-GlcNAcOC8H17 disaccharide derivatives bearing different hydroxylated alkyl chains, with or without sulfate groups at C-4 and/or C-6 positions of the GlcNAc unit, have been synthesized and tested as inhibitor