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In an article, published in an article, once mentioned the application of 10343-06-3, Name is 2,3,4,6-Tetra-o-acetyl-D-glucopyranose,molecular formula is C14H20O10, is a conventional compound. this article was the specific content is as follows.Application In Synthesis of 2,3,4,6-Tetra-o-acetyl-D-glucopyranose

Glycosyl chlorides and bromides can be rapidly converted to glycals in high yield by reaction with (Cp2Ti[III]Cl)2. This reagent tolerates a wide range of common carbohydrate protecting groups, including silyl ethers, acetals, and esters; the methodology provides a general route for the preparation of glycals substituted with both acid- and base-labile functionality. A reaction mechanism is proposed that is based on heteroatom abstraction to give an intermediate glycosyl radical. This radical reacts with a second equivalent of Ti(III) to yield a glycosyltitanium(IV) species. beta-Heteroatom elimination from the glycosyltitanium(IV) complex gives the glycal.

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Novel inhibitors of Ras protein activation have been found, containing a bicyclic core derived from D-arabinose and benzyl and phenylhydroxylamine moieties. NMR studies (trNOE, saturation-transfer difference, STD) of the binding between these molecules and human p21 h-Ras are reported. A pharmacophore mapping indicates that both the benzyl and the phenylhydroxylamine moieties are essential for protein binding. Molecules lacking one of these groups were synthesized and tested to confirm this hypothesis, and no interaction with Ras in vitro, nor biological activity in mammalian cells was observed. Our studies led to the development of molecules that selectively inhibit Ras-dependent cellular growth in mammalian cells. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.

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An efficient and novel methodology to access phenolic glycosides has been established by using copper-mediated coupling reaction of aryl boronic acids with hemiacetals. The reaction takes place normally in the presence of Cu(OAc)2 (1.0 equiv.) and pyridine (2.0 equiv.) at 40 C. This protocol distinguishes itself by wide substrate scope, operational simplicity and giving rise to a myriad of phenolic glycosides in good to excellent yields.

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A series of novel guanidinoglycosides was successfully synthesized. This was accomplished with the use of Mitsunobu conditions as a strategy to convert the glycopyranose anomeric hydroxy group to give the corresponding substituted masked guanidines in high yields. Subsequent deprotection and coupling with Fmoc protected beta-amino acid, afforded a series of N,N?-substituted-methyl-isothioureas. Cleavage of Fmoc followed by concomitant cyclization was achieved with a catalytic amount of DBU to give the guanidinoglycosides.

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Tetrahydropyran – Wikipedia,
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In an article, published in an article, once mentioned the application of 10343-06-3, Name is 2,3,4,6-Tetra-o-acetyl-D-glucopyranose,molecular formula is C14H20O10, is a conventional compound. this article was the specific content is as follows.Quality Control of: 2,3,4,6-Tetra-o-acetyl-D-glucopyranose

A number of new glycosyl donors, O-(1-phenyl-1H-tetrazol-5-yl) glycosides, are prepared from the corresponding hemiacetals, commercially available 5-chloro-1-phenyl-1H-tetrazole (2), and tetrabutylammonium fluoride (Bu4NF) in either THF or DMF. The mild reaction conditions are compatible with a variety of protecting groups. The glycosyl donors are treated with hydrogen fluoride-pyridine complex (HF ¡¤ py) to rapidly provide glycosyl fluorides in good-to-excellent yields, apparently by a (single or double) S(N)2 mechanism as studied by both 1H- and 19F-NMR spectroscopy. Under acidic conditions, glycosyl fluorides equilibrate partially or completely, equilibration requiring a large excess of HF ¡¤ py.

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We report the simultaneous reduction of the 2-position and oxidation of the anomeric position in several protected furanosyl and pyranosyl sugar derivatives, mediated through NHC catalysis. This reaction allows the one-step access to highly valuable 2-deoxy-sugars from abundant 2-oxygenated sugar derivatives. Georg Thieme Verlag Stuttgart ¡¤ New York.

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Lanthanide triflates, especially Nd(OTf)3, efficiently catalyze the regioselective transesterification of anomeric acetates. This method offers an efficient solution for the otherwise difficult removal of methyl uronates anomeric acetates as well as a green alternative to published protocols since the lanthanide catalysts are non-toxic and may be easily recycled and reused.

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Using a halogen bond (XB) donor and Schreiner’s thiourea as cooperative catalysts, various amides, including the asparagine residues of several peptides, were directly coupled with glycosyl trichloroacetimidates to give unique N-acylorthoamides in good yields. Synthetic applications of N-acylorthoamides, including rearrangement to the corresponding beta-N-glycoside, were also demonstrated.

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Tetrahydropyran – Wikipedia,
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In an article, published in an article, once mentioned the application of 10343-06-3, Name is 2,3,4,6-Tetra-o-acetyl-D-glucopyranose,molecular formula is C14H20O10, is a conventional compound. this article was the specific content is as follows.Application In Synthesis of 2,3,4,6-Tetra-o-acetyl-D-glucopyranose

The development of an efficient and practical process for the preparation of Sergliflozin etabonate (1), a prodrug of a novel selective low-affinity Na+-dependent glucose cotransporter (SGLT2) inhibitor, Sergliflozin (2), is described. Its development required a suitable process for large-scale manufacturing. We established a chromatography-free approach for 2-[(4-methoxyphenyl)methyl]phenol (5), the efficient O-glycosylation of 5 with penta-O-acetyl-beta-D-glucopyranose (7) without using a trichloroacetimidate intermediate (9), and efficient reaction conditions to introduce an ethoxycarbonyl group onto the primary alcohol of 2 with high selectivity. This process provided 1 with a 45% overall yield from anisole (10).

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Tetrahydropyran – Wikipedia,
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Polystyrene-supported strong organic bases are highly efficient reagents for the solution-phase synthesis of glycosyl trichloroacetimidates, affording quantitative yields of pure products in short reaction times after simple filtration and evaporation. Although efficiency of the different bases varies with substrate structure, polymer-bound 1,8-diazabicyclo[5.4.0]undec-7-ene was found to give the best results for all the substrates tested.

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