Our Top Choice Compound: C14H20O10

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A new and efficient method for catalytic hydrolysis of thioglycosides was successfully developed. Various thioglycosides were smoothly hydrolyzed to afford the corresponding 1-hydroxy sugars in high yields. The hydrolysis of disaccharides was took place smoothly without accompanying no anomerization of existing glycosidic bond.

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Photo-induced radical addition of acetylated alpha-D-glucopyranosyl bromide (1) to acrylonitrile or diethyl vinylphosphonate, in the presence of catalytic amounts of tri-n-butyltin chloride and sodium (or tetra-n-butylammonium) cyanoborohydride in excess, allowed efficient preparations of alpha-configurated nonononitrile and 2-(alpha-D-glucopyranosyl)-ethylphosphonate (79, 70% yields, respectively). These conditions led to 2-(alpha-D-manno-, and galactopyranosyl)-ethylphosphonates in 68 and 76% yields. Similarly, radical addition of acetylated 1-bromo-beta-D-glucopyranosyl chloride (2) to acrylonitrile or diethyl vinylphosphonate afforded mainly intermediate chlorides which, upon radical reduction with excess tri-n-butyltin hydride, afforded the corresponding beta anomers (40 and 38%, respectively) by sequential C-C and C-H bond formation. Stereocontrol relies on the alpha-stereoselective quenching of D-glycopyranos-1-yl radicals. We found also that UV light irradiation of 1 with excess NaBH3CN in tert-butanol afforded either 1,3,4,6-tetra-O-acetyl-2-deoxy-alpha-D-arabino-hexopyranose (65% after crystallization) or, when 10% mol thiophenol was added, 2,3,4,6-tetra-O-acetyl-1,5-anhydro-D-glucitol (79%). These are simple, tin-free, and easily controlled conditions, which compare well with known preparations of these reduced sugars.

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Reactions catalyzed within inorganic and organic materials and at electrochemical interfaces commonly occur at high coverage and in condensed media, causing turnover rates to depend strongly on interfacial structure and composition. 10343-06-3, Name is 2,3,4,6-Tetra-o-acetyl-D-glucopyranose, molecular formula is C14H20O10. In a Patent,once mentioned of 10343-06-3, HPLC of Formula: C14H20O10

The present disclosure provides novel sweetener compositions comprising a compound having a structure according to Formula I: wherein R1, R2, R3, and R4 are described herein. Also provided are methods of modulating sweetness profile of a product by adding a compound of Formula I to the product, such as a beverage product or a food product. For example, the compound described herein can be added to increase the overall sweetness of a nutritive sweetener sweetened beverages; decrease the sweetness time-of-onset for high potency sweeteners such as rebaudioside A; decreasing bitter, metallic and licorice off-notes of high potency sweeteners; and improve the sweet quality of sweetened products.

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Phenethyl glycosides having phenolic or methoxy functions at benzene rings are substances widely occurring in nature. This kind of compounds has been shown to have anti-oxidant, anti-inflammatory, and anticancer activities. However, some of them are not naturally abundant, thus the synthesis of such molecules is desirable. In this paper, natural phenethyl glycosides 3 and 4 were first totally synthesized from easily available materials with overall yields of 50.5% and 40.1%, respectively. And a new synthetic route to obtain natural phenethyl glycoside 2 in 46.2% yield was also described.

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Treatments of fully acetylated sugars with bis(tributyltin) oxide in toluene at reflux, and with potassium cyanide or potassium hydroxide, or both, in mixtures of tetrahydrofuran and 2-propanol were found to be effective for regioselective 1-O-deacetylation of fully acetylated sugars.

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The relative rate of hydrolysis of an alpha/beta anomeric pair of glycosides is generally considered to provide insight into various factors that influence anomeric reactivity. However the fact that such hydrolyses are usually carried out with aqueous acids severely limits the range of substrates that can studied. This limitation is overcome with n-pentenyl glycosides (NPGs) which are hydrolyzed under neutral, oxidative conditions. A procedure is described in which a pair (e.g. alpha1/beta1, alpha1/beta2, beta1/beta2,etc.) of NPGs is made to compete for an insufficient amount of N-bromosuccinimide, the relative rates of reaction being determined from HPLC peak heights of the unreacted starting materials. Some commonly used acid labile protecting groups, e.g. cyclic acetals and acetyl, are shown to exert profound effects upon relative and absolute rates of anomeric activation.

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Transformation of 1-O-unprotected glucose and galactose derivatives (1a-d) into O-glycosyl dichloro-cyanoacetimidates (2a-d) was performed with dichloro-cyanoacetonitrile in the presence of DBU as base. Reaction with different acceptors (3a-d) under TMSOTf catalysis afforded glycosides 4 in high yields. Competition experiments with O-glucopyranosyl trichloroacetimidate 10a, bearing a 4-tert-butylbenzyl group at 6-O, and O-glucopyranosyl dichloro-cyanoacetimidate 10b, bearing a 4-methylbenzyl group at 6-O, displayed similar reactivities for these two types of glycosyl donors.

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The invention relates to the identification of sterol glucoside toxins, and provides methods for detecting and detoxifying the compounds, as well as therapeutic methods for treating subjects exposed to such toxins. In alternative embodiments, the toxins may for example include beta-sitostrol-beta-D-glucoside (5-cholesten-24b-ethyl-3b-ol-D-glucoside) or cholesterol glucoside (5-cholesten-3b-ol-3b-D-glucoside).

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The X-ray analyses of 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyran-osyl fluoride, C14H19FO9, (I), and the corresponding maltose derivative 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl-(1?4)- 2,3,6-tri-O-acetyl-alpha-D-glucopyran-osyl fluoride, C26H 35FO17, (II), are reported. These add to the series of published alpha-glycosyl halide structures; those of the Peracetylated alpha-glucosyl chloride [James & Hall (1969). Acta Cryst. A25, S196] and bromide [Takai, Watanabe, Hayashi & Watanabe (1976). Bull. Fac. Eng. Hokkaido Univ. 79, 101-109] have been reported already. In our structures, which have been determined at 140 K, the glycopyranosyl ring appears in a regular 4C1 chair conformation with all the substituents, except for the anomeric fluoride (which adopts an axial orientation), in equatorial positions. The observed bond lengths are consistent with a strong anomeric effect, viz. the C1-O5 (carbohydrate numbering) bond lengths are 1.381 (2) and 1.381 (3) A in (I) and (II), respectively, both significantly shorter than the C5-O5 bond lengths, viz. 1.448 (2) A in (I) and 1.444 (3) A in (II).

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Alcohols were protected by esterification with new protecting reagents, 2-<2-(arylmethyloxy)ethyl>benzoic acids and the esters were chemoselectively deprotected in a proximately assisted manner even in the presence of acetyl, levulinyl, and silyl groups.

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