181115-83-3

Upstream product

• 4753-07-5 α-hepta-O-acetylmaltosyl bromide 
• 113842-87-8 allyl α-D-glucopyranosyl-(1->4)-β-D-glcopyranoside 
• 97777-13-4 allyl O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1<*>4)-2,3,6-tri-O-acetyl-β-D-gluco-pyranoside 
• 181115-77-5 allyl 2,3,6-tri-O-4-methoxybenzyl-4-O-(2,3-di-O-4-methoxybenzyl-4,6-O-4-methoxybenzylidene-α-D-glucopyranosyl)-β-D-glucopyranoside 
• 3616-19-1 1,2,3,6,2',3',4',6'-octa-O-acetylmaltose 
• 181115-76-4 allyl 4-O-(4,6-O-4-methoxybenzylidene-α-D-glucopyranosyl)-β-D-glucopyranoside 
• 22352-19-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl acetate 
• 4753-07-5 2,3,6,2',3',4',6'-hepta-O-acetyl-α-D-maltosyl bromide 

Downstream Products

• 181115-84-4 allyl 2,3,6-tri-O-4-methoxybenzyl-4-O-(4-O-acetyl-2,3,6-tri-O-4-methoxybenzyl-α-D-glucopyranosyl)-β-D-glucopyranoside 
• 181115-86-6 4-(methoxycarbonyl)benzyl 2,3,6-tri-O-4-methoxybenzyl-4-O-(4-O-acetyl-2,3,6-tri-O-4-methoxybenzyl-α-D-glucopyranosyl)-α-D-glucopyranoside 
• 181115-87-7 4-(methoxycarbonyl)benzyl 2,3,6-tri-O-4-methoxybenzyl-4-O-(2,3,6-tri-O-4-methoxybenzyl-α-D-glucopyranosyl)-α-D-glucopyranoside 
• 181115-80-0 4-(carboxy)benzyl 2,3,6-tri-O-4-methoxybenzyl-4-O-(2,3,6-tri-O-4-methoxybenzyl-α-D-glucopyranosyl)-α-D-glucopyranoside 
• 181115-89-9 Benzoic acid (2R,3R,4S,5R,6R)-6-[(2R,3R,4S,5R,6R)-6-allyloxy-4,5-bis-(4-methoxy-benzyloxy)-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-yloxy]-4,5-bis-(4-methoxy-benzyloxy)-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-yl ester 

Relevant academic research and scientific papers

Carbohydrate-carbohydrate interactions in water with glycophanes as model systems

The synthesis and conformational properties of glycophanes 2 and 3 (cyclodextrin-cyclophane hybrid receptors containing two maltose units linked by (4-hydroxymethyl) benzoic acid spacer) are described. The binding properties in water of these receptors with a series of 4-nitrophenyl glycosides with α- and β-configurations at the anomeric center have been studied using 1H NMR spectroscopy and molecular mechanics calculations. A comparison of these properties with those of glycophane 1 (an α,α-trehalose containing glycophane) and α-cyclodextrin (αCD) using the same glycosides shows the existence of a stabilizing contribution to the free energy of binding in the case of of glycophanes but not in the case of the αCD system. This contribution is due to carbohydrate-carbohydrate interactions between both host and guest lipophilic sugar surfaces. Glycophanes 1, 2, and 3 show similar α/β selectivity on binding the ligands, despite the great flexibility of 3 related to 1 and 2. Parallels are drawn between the thermodynamic behavior of these model systems and that proposed for sugar- protein interactions.

Two interconverting glycophanes from maltose

Two new glycophanes, 1 and 3, that interconvert through transesterification in water at room temperature are presented. The synthesis, properties of interconvertion and preliminary binding and conformational studies of these macrocycles are also described.