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Showing 1 to 13 of 13 for “"Trichloroacetimidate"”.
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Trichloroacetimidates as Alkylating Reagents and Their Application in the Synthesis of Pyrroloindoline Natural Products and Synthesis of Small Molecule Inhibitors of Src Homology 2 Domain- Containing Inositol Phosphatase (SHIP)
<p>Trichloroacetimidates are known to be excellent alkylating agents when activated by a catalytic amount of a Brønsted or Lewis acid. Work described herein involved taking advantage of the favorable reactivity of trichloroacetimidates to establish several different synthetic protocols, including …
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Trichloroacetimidates as Alkylating Reagents in C-N Bond Formation and Synthesis of Aminosteroid and Quinoline Inhibitors of Src Homology 2 Domain-Containing Inositol Phosphatase (SHIP)
<p>Trichloroacetimidates have frequently been used in the formation of glycosidic bonds and other ethers, which is especially useful for the introduction of ether protecting groups. Trichloroacetimidates have also been used as electrophiles in Friedel-Crafts alkylation reactions. The formation of …
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Synthesis of Hetero-chitooligosaccharides
… of the amines. The donor was activated as the trichloroacetimidate in order to form the β-linkages. Glycosylation in the presence of trimethylsilyl trifluoromethanesulfonate, followed by N- and O-deprotection furnished chitobioses and chitotetraoses in good yields.
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Solution and solid phase synthesis of N,N'-diacetyl chitotetraoses
… through neighboring group participation and the trichloroacetimidate approach was utilized for the donor. Monomeric, dimeric acceptors and donors have been prepared by utilizing the Z and PNZ groups and coupling between the appropriate donor and acceptors in the presence of Lewis acid yielded the …
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Thioetherification and Etherification Utilizing Trichloroacetimidates Under Thermal Conditions & Progress Towards an Efficient Synthesis of AQX-1125
… solely under thermal conditions utilizing trichloroacetimidates.</p> <p>The alkylation of thiols by the direct displacement of trichloroacetimidates has been accomplished under thermal conditions (heating in refluxing THF). These reactions proceed to the corresponding thioetherification …
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Toward the Synthesis of CAY-1, an Antifungal Steroidal Saponin
… ƒÀ-(1¨4) linkage was achieved using a disarmed trichloroacetimidate glucosyl donor.
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Formation of Pyrroloindolines and Alkylation of N-heterocycles With Trichloroacetimidates and Synthesis of Quinoline Based Small Molecule Inhibitors of Ghrelin O-acyltransferase (goat)
… properties. Recently we have focused on using trichloroacetimidates for the synthesis of these fascinating molecules. Trichloroacetimidates can be used an electrophilic source of an alkyl group to form the pyrroloindoline directly from tryptamine derivatives. In this manner …
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N9 Alkylation and Glycosylation of Purines; A Practical Synthesis of 2-Chloro-2'-deoxyadenosine
… the activation energy by introduction of trichloroacetimidate at the anomeric carbon.</p> <p>(b) 6-Heteroaryl functions [6-(1,2,4-triazol-4-yl) and 6-(imidazol-1-yl)] were introduced into purine derivatives for regioselective N9 alkylation. The regiospecificity of alkylation mainly results …
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Reactions for rapid access to C3a oxygenated pyrroloindolines and its application towards a novel route to pestalazine A
… in this work simply heating diarylmethyl trichloroacetimidates with the allyltributylstannane gives easy access to these systems. Electron rich benzylic trichloroacetimidate systems gave the best results, where excellent yields are achieved just by refluxing the reactants together in …
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A Modular Approach to Highly Functionalized Indole Derivatives and Syntheses of Tryptamine-based SHIP Inhibitors
… account of reactions of glycosyl or alkyl trichloroacetimidates with various indole derivatives substituted at N-, 2- and 3- position. While Friedel Crafts reactions of indoles with trichloroacetimidates are known, regioselectivity of these reactions is not very clear. The relative utility …
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CONVENIENT ETHERIFICATION USING TRICHLOROACETIMIDATES AND SYNTHESIS OF AMINOSTEROID SHIP INHIBITORS
… systems. The most common imidate system, the trichloroacetimidate, is often utilized for the installation of ethers under Lewis acid catalyzed conditions. Given their ready availability, a reevaluation of the reactivity of alcohols and trichloroacetimidates has been undertaken. In many cases, …
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Exploration of Carbon-oxygen and Carbon-nitrogen Bond Formation Utilizing Trichloroacetimidates and Investigations of New Reactions Mediated By Oxoammonium Salts
… bulky groups onto one of the phenolic oxygens. Trichloroacetimidates are also shown to be useful reactions for the synthesis of esters. These reagents proceeded through a symbiotic activation pathway. Under these conditions sensitive substrates did not decompose, which often is observed with …
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Chemistry of hydroxycinnamate esters and their role as precursors to Dekkera produced off-flavour in wine.
… (21 and 22), esterifying with a prepared trichloroacetimidate glucosyl donor sequence, though purification of the glucose esters resulted in undesired chemical transformations. It was found that photoisomerisation of the glucose esters could be prevented via synthesis under red light, …