273749-60-3

Upstream product

• 13992-16-0 (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(phenylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 83-87-4 D-glucose pentaacetate 
• 108-98-5 thiophenol 
• 13992-16-0 phenyl 2,3,4,6-tetra-O-acetyl-1-thio-α,β-D-glucopyranoside 
• 492-61-5 β-D-glucose 
• 2186-92-7 p-Anisaldehyde dimethyl acetal 
• 2936-70-1 (2R,3S,4S,5R,6S)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol 

Downstream Products

• 556039-06-6 (2R,4aR,6S,7R,8R,8aR)-8-tert-butyldimethylsilyloxy-2-(4-methoxyphenyl)-6-phenylthiohexahydropyrano[3,2-d][1,3]dioxin-7-ol 
• 273749-73-8 (2R,4aR,6R,7R,8R,8aS)-6-((2R,4aR,6R,7R,8R,8aS)-7-Azido-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol 
• 273749-62-5 methyl O-(2,3-di-O-pivaloyl-4,6-O-(4-methoxybenzylidene)-β-D-glucopyranosyl)-(1->3)-2-azido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 
• 273749-64-7 methyl O-(2,3-di-O-benzyl-6-O-(4-methoxybenzyl)-β-D-glucopyranosyl)-(1->3)-2-azido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 
• 273749-63-6 methyl O-(2,3-di-O-benzyl-4,6-O-(4-methoxybenzylidene)-β-D-glucopyranosyl)-(1->3)-(2-azido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside) 
• 273749-68-1 6-(7-acetylamino-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-4,5-bis-benzyloxy-3-(4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-carboxylic acid 
• 273749-67-0 methyl O-(3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->4)-(2,3-di-O-benzyl-6-O-(4-methoxybenzyl)-β-D-glucopyranosyl)-(1->3)-(4,6-O-benzylidene-2-acetamido-2-deoxy-β-D-glucopyranoside) 
• 273749-66-9 methyl O-(3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl)-(1->4)-(2,3-di-O-benzyl-6-O-(4-methoxybenzyl)-β-D-glucopyranosyl)(1->3)-2-azido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 
• 556039-07-7 phenyl 2-O-allyl-3-O-^tbutyldimethylsilyl-4,6-O-p-methoxybenzylidene-1-thio-β-D-glucopyranoside 
• 556039-03-3 phenyl 2-O-allyl-4-O-p-methoxybenzyl-1-thio-β-D-glucopyranoside 
• 273749-71-6 phenyl 2,3-di-O-pivaloyl-4,6-O-(4-methoxybenzylidene)-1-thio-β-D-glucopyranoside 

Relevant academic research and scientific papers

Chemical Synthesis of Modified Hyaluronic Acid Disaccharides

Herein we report a chemical synthesis towards new modified hyaluronic acid oligomers by using only commercially available d-glucose and d-glucosamine hydrochloride. The various protected hyaluronic acid disaccharides were synthesized bearing new functional groups at C-6 of the β-d-glucuronic acid moiety with a view to structure-related biological activity tests. The orthogonal protecting group pattern allows ready access to the corresponding higher oligomers. Also, 1H NMR studies of the new derivatives demonstrated the effect of the various functional groups on the intramolecular electronic environment.

Efficient one-pot per-: O -acetylation-thioglycosidation of native sugars, 4,6- O -arylidenation and one-pot 4,6- O -benzylidenation-acetylation of S -/ O -glycosides catalyzed by Mg(OTf)2

A sequential one-pot per-O-acetylation-S-/O-glycosidation of native mono and disaccharides under solvent free conditions using 0.5 mole% of Mg(OTf)2 as a non-hygroscopic, recyclable catalyst is reported. Regioselective 4,6-O-arylidenation of glycosides and thioglycosides with benzaldehyde or p-methoxybenzaldehyde dimethyl acetal is catalyzed by 10 mole% of Mg(OTf)2 to produce the corresponding 4,6-O-arylidenated product in high yields. Mg(OTf)2 can also mediate sequential one-pot benzylidenation-acetylation of mono and disaccharide based glycosides and thioglycosides in high yield.

Synthesis of the non-reducing end trisaccharide of the antithrombin-binding domain of heparin and its bioisosteric sulfonic acid analogues

A glucoronic acid-containing trisaccharide related to the antithrombin-binding DEFGH domain of heparin and its methanesulfonic acid analogues were synthesized. Trisaccharides without sulfonic acid content or possessing a sulfonatomethyl moiety at position

FeCl3 mediated arylidenation of carbohydrates

Glycosides and thioglycosides based on monosaccharides in reaction with benzaldehyde dimethylacetal or p-methoxybenzaldehyde dimethyl acetal undergo FeCl3-catalyzed (20 mol %) regioselective 4,6-O-arylidenation producing the corresponding acetals in high yields. FeCl3 also mediates acetalation of glycosides and thioglycosides of cellobiose, maltose, and lactose affording the corresponding 4′,6′-O-benzylidene acetals, which were isolated after their acetylation in situ with acetic anhydride and pyridine. The combined yields (two steps) of these final products are also high (61-84%). The procedure is applicable to a wide variety of functional groups including -OBn.

Synthesis of sulfonic acid analogues of the non-reducing end trisaccharide of the antithrombin binding domain of heparin

Three sulfonic acid trisaccharides related to the antithrombin-binding DEFGH domain of heparin were synthesised. Trisaccharides carrying the sulfonatomethyl moiety at position 2 or 6 were prepared in high yields by [DE+F] couplings using the same disaccha

Carbohydrate-based scaffolds for the generation of sortiments of bioactive compounds

The polyfunctionality and conformational rigidity of carbohydrates make this class of compounds ideal scaffolds for the production of sortiments1 of bioactive compounds. Examples of carbohydrate-derived peptidomimetics of biological interest, such as somatostatin agonists and integrin antagonists, are presented. In order to have access to solid phase supported sortiments of compounds, orthogonally protected or unprotected carbohydrates were linked to polymers and reacted in the solid phase employing different regioselective strategies. Original bicyclic and tricyclic glycidic scaffolds were easily obtained starting from natural sugars such as D-arabinose and D-fructose. Manipulation of these conformationally blocked compounds afforded different carbohydrate-based derivatives, among which azidoacids are useful precursors of β-turn peptidomimetics.

Synthesis of two hyaluronan trisaccharides

(equation presented) The synthesis of two hyaluronan trisaccharides, methyl O-(β-D-glucopyranosyluronic acid)-(1,3)-O(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1,4)-O-β-D- glucopyranosiduronic acid and methyl O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1,4)-O-β-D- glycopyranosyluronic acid)-(1,3)-O-(2-acetamido-2-deoxy-β-D-glucopyranoside, are described. Construction of the target molecules was achieved though a combination of the phenyl sulfoxide and trichloroacetimidate glycosylation methodologies. This is the first report on the synthesis of the β-methyl derivatives, which represent the smallest fragments that incorporate all the structural features of polymeric hyaluronan.