Complexation of hexosammonium ions: evidence for contributions from OH···OH hydrogen bonds in a hydroxylic medium was written by Savage, Paul B.;Gellman, Samuel H.. And the article was included in Journal of the American Chemical Society in 1993.Application In Synthesis of (2S,3S,4R,5S,6R)-3-Acetamido-6-(acetoxymethyl)tetrahydro-2H-pyran-2,4,5-triyl triacetate This article mentions the following:
The synthesis and complexation properties of macrocycle 3 (I) are described. Simpler macrocycle 1 (II) was previously shown to bind primary ammonium ions in CDCl3/CD3OD mixtures; the authors now report that 3 binds hexosammonium ions in 10 volume% CD3OD in CDCl3. The following Ka values were measured for 3 and several hexosamine-HCl as their (p-tert-butylbenzyl)thioglycoside derivatives: β-glucosammonium (3,000 M-1), α-glucosammonium (2,800 M-1), β-galactosammonium (1,400 M-1), β-mannosammonium (1,000 M-1), α-mannosammonium (2,200 M-1). Macrocycle 3 binds cyclohexylammonium chloride with a Ka of only 570 M-1, i.e., significantly less strongly than the hexosammonium ions. In contrast, macrocycle 1 binds cyclohexylammonium chloride more tightly than the hexosammonium ions (e.g., 1,700 M-1 for 1 + cyclohexylammonium chloride vs. 870 M-1 for 1 + β-glucosammonium derivative). Thus, interactions between the peripheral hydroxyl groups of macrocycle 3 and the monosaccharide hydroxyls contribute to the stability of the bound state. This observation is particularly interesting in light of the fact that the solvent (2.5 M CD3OD) contains ample hydroxyl groups for competitive H-bonding interaction. In the experiment, the researchers used many compounds, for example, (2S,3S,4R,5S,6R)-3-Acetamido-6-(acetoxymethyl)tetrahydro-2H-pyran-2,4,5-triyl triacetate (cas: 6730-10-5Application In Synthesis of (2S,3S,4R,5S,6R)-3-Acetamido-6-(acetoxymethyl)tetrahydro-2H-pyran-2,4,5-triyl triacetate).
(2S,3S,4R,5S,6R)-3-Acetamido-6-(acetoxymethyl)tetrahydro-2H-pyran-2,4,5-triyl triacetate (cas: 6730-10-5) belongs to esters. Esters are widespread in nature and are widely used in industry. In nature, fats are in general triesters derived from glycerol and fatty acids. Esters are responsible for the aroma of many fruits, including apples, durians, pears, bananas, pineapples, and strawberries. Esters are more polar than ethers but less polar than alcohols. They participate in hydrogen bonds as hydrogen-bond acceptors, but cannot act as hydrogen-bond donors, unlike their parent alcohols. This ability to participate in hydrogen bonding confers some water-solubility.Application In Synthesis of (2S,3S,4R,5S,6R)-3-Acetamido-6-(acetoxymethyl)tetrahydro-2H-pyran-2,4,5-triyl triacetate
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