Category: 6730-10-5

Anomeric equilibria in derivatives of amino sugars. Nuclear magnetic resonance studies on acetylated amino sugars and specifically deuterated analogs was written by Horton, Derek;Hughes, Jack B.;Jewell, Jon S.;Philips, Kerstin D.;Turner, William Nelson. And the article was included in Journal of Organic Chemistry in 1967.Formula: C16H23NO10 This article mentions the following:

Acetylation of derivatives of 2-amino-2-deoxy-D-glucose and 2-amino-2-deoxy-D-mannose with Ac2O-d6 permitted definitive assignment of the signal for the N-Ac Me group in the N.M.R. spectra of the pyranose pentaacetates of the 2 amino sugars, and some related derivatives The anomeric compositions of the mixtures formed by acetylation of the amino sugars, and a number of simple sugars, with Ac2O in pyridine, were investigated. Aryl substituents in acetylated sugar derivatives are shown to cause shielding of certain Ac groups, with the result that, in CHCl3-d, the N.M.R. signals of these Ac groups are observed at unusually high field. 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: 6730-10-5Formula: C16H23NO10).

(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 also usually derived from carboxylic acids. It may also be obtained by reaction of acid anhydride or acid halides with alcohols or by the reaction of salts of carboxylic acids with alkyl halides. Cyclic esters are called lactones, regardless of whether they are derived from an organic or inorganic acid. One example of an organic lactone is γ-valerolactone.Formula: C16H23NO10

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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 K_a 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 K_a 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

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

2,3-Carbamate mannosamine glycosyl donors in glycosylation reactions of diacetone-D-glucose. An experimental and theoretical study was written by Morelli, Laura;Legnani, Laura;Ronchi, Silvia;Confalonieri, Laura;Imperio, Daniela;Toma, Lucio;Compostella, Federica. And the article was included in Carbohydrate Research in 2021.SDS of cas: 6730-10-5 This article mentions the following:

The role of the cyclic 2,3-N,O-carbamate protecting group in directing the selectivity of mannosylation reactions of diacetone-D-glucose, promoted by BSP/Tf₂O via α-triflate intermediates, has been investigated through a combined computational and exptl. approach. DFT calculations were used to locate the transition states leading to the α or β anomers. These data indicate the preferential formation of the β-adduct with mannosyl donors either equipped with the 4,6-O-benzylidene protection or without it. The synthetic results confirmed this preference, showing in both cases an α/β selectivity of 4:6. This highlights a role for the 2,3-N,O-carbamate in sharp contrast with what described in the case of 2,3-O-carbonate mannosyl donors. 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: 6730-10-5SDS of cas: 6730-10-5).

(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 perform as high-grade solvents for a broad array of plastics, plasticizers, resins, and lacquers, and are one of the largest classes of synthetic lubricants on the commercial market. Polyesters are important plastics, with monomers linked by ester moieties. Many esters have the potential for conformational isomerism, but they tend to adopt an s-cis (or Z) conformation rather than the s-trans (or E) alternative, due to a combination of hyperconjugation and dipole minimization effects. The preference for the Z conformation is influenced by the nature of the substituents and solvent, if present. Lactones with small rings are restricted to the s-trans (i.e. E) conformation due to their cyclic structure.SDS of cas: 6730-10-5

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics