848863-34-3

Upstream product

• 150-76-5 4-methoxy-phenol 
• 3616-19-1 1,2,3,6,2',3',4',6'-octa-O-acetylmaltose 
• 6920-00-9 D-maltose octaacetate 
• 108-24-7 acetic anhydride 

Downstream Products

• 848863-40-1 p-methoxyphenyl 2,3-di-O-benzoyl-6-O-tert-butyldimethylsilyl-4-O-(2,3-di-O-benzoyl-4,6-O-benzylidene-α-D-glucopyranosyl)-β-D-glucopyranoside 
• 848863-41-2 p-methoxyphenyl 2,3-di-O-benzoyl-4-O-(2,3-di-O-benzoyl-4,6-O-benzylidene-α-D-glucopyranosyl)-β-D-glucopyranoside 
• 848863-39-8 p-methoxyphenyl 4-O-(4,6-O-benzylidene-α-D-glucopyranosyl)-6-O-tert-butyldimethylsilyl-β-D-glucopyranoside 
• 848863-37-6 4-methoxyphenyl (4,6-O-benzylidene-α-D-glucopyranosyl)-(1→4)-β-D-glucopyranoside 
• 863561-13-1 p-methoxyphenyl 6-O-triphenylmethyl-4-O-(6-O-triphenylmethyl-α-D-glucopyranosyl)-β-D-glucopyranoside 
• 863561-23-3 p-methoxyphenyl 2,3,6-tri-O-benzyl-4-O-(2,3-di-O-benzyl-α-D-glucopyranosyl)-β-D-glucopyranoside 

Relevant academic research and scientific papers

Solvent-Free Glycosylation from per-O-Acylated Donors Catalyzed by Methanesulfonic Acid

The huge importance of carbohydrates and their derivatives in biomedical and industrial applications call for the development of streamlined and sustainable procedures for their synthetic elaboration. Here reported a novel glycosylation method based on direct activation of readily available per-O-acylated (acetylated or benzoylated) donors, promoted under air by methanesulfonic acid as a cheap and green catalyst in the absence of any solvent. Besides the beneficial avoidance of toxic and polluting organic solvents, these conditions were found critical for activating such poorly reactive donors with a very small catalyst loading (only 5 mol %), instead of stoichiometric Lewis acid promoters typically employed. Desired glycosides were quickly obtained, in most cases with high 1,2-trans stereoselectivity. Other main advantages over reported glycosylations with similar donors are the limited stoichiometric excess of the acceptor (or the donor), the easy applicability and low cost of the procedure and the wide target scope, also covering the synthesis of disaccharides and other non-trivial glycosides with applicable potential.

Lanthanum trifluoromethane-sulfonate-catalyzed facile synthesis of per-O-acetylated sugars and their one-pot conversion to S-aryl and O-alkyl/aryl glycosides

Lanthanum trifluoromethanesulfonate-catalyzed solvent-free per-O-acetylation with stoichiometric acetic anhydride proceeds in high yield (95%-99%) to afford exclusively pyranose products as anomeric mixtures. Subsequent anomeric substitution employing borontrifluoride etherate and thiols or alcohols furnished the corresponding 1,2-trans-linked thioglycosides and O-glycosides, respectively, in good to excellent overall yield (75%-85%). Alternatively, reaction of free sugars in neat alcohol employing the same catalyst at elevated temperature gives the corresponding 1,2-cis-linked O-glycosides (along with 1,2-trans-linked glycosides as minor product) in good yield (73%-80%). Anomeric mixtures of compounds thus produced were characterized as their per-O-acetylated derivatives.

Synthesis of triazole-linked pseudo-starch fragments

Rapid assembly of starch fragment analogues was achieved using 'click chemistry'. Specifically, a pentadecasaccharide and two hexadecasaccharide mimics containing two parallel maltoheptaosyl chains linked via [1,2,3]-triazoles to glucose or maltose core w

"Click chemistry" en route to pseudo-starch

The application of click chemistry based on cycloaddition of substituted azide and alkynes to the synthesis of well-defined branched oligosaccharide related to starch was discussed. This modular approach allowed the construction of a number of [1,2,3]-tri

Exploiting an aromatic aglycone as a reporter of glycosylation stereochemistry in the synthesis of 1,6-linked maltooligosaccharides

Analysis of glycosylation stereoselectivity in the synthesis of branched maltooligosaccharides is hampered by poor spectral dispersion due to the repetitive nature of the saccharide chain and overlap of sugar H-1 signals with benzylic proton signals from