39093-93-1, Thiomorpholine 1,1-dioxide is a Thiomorpholine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated
B. Synthesis of 5?-O-DMT-3?-O-[methyl-(N,N-diisopropyl)]-phosphoramidite-2?-O-thiomorpholino-1, 1-dioxidethionocarbamateuridine. 3?-5?-tetraisopropyldisiloxane Uridine (ChemeGenes), 10 mmol, 4.8 grams was dissolved in 100mls of anhydrous acetonitril in a 500 ml roundbottom flask fitted with a serum stopper. To the reaction 1.9 grams of1, 1?-thiocarbonyldiimidazole (Aldrich) was added with 0.2 grams of 4-(dimethyl)aminopyridine. The reaction washeated using a heat gun and stirred until the reagents had dissolved and the solution was clear. The reaction wasallowed to stir overnight (12 hours). After 12 hours, the reaction mixture was a slurry of crystals. The crystals wereisolated by filtration through a medium sintered glass funnel. The product was washed with cold acetonitrile anddried under vacuum. TLC analysis confirmed that the product was a single species giving 5.97 grams of product(100percent) ESI-Q-TOF mass spectroscopy analysis confirmed the product as the 5?,3?-O-(tetraisopropyldisiloxane-1,3-diyl)-2?-thionoimidazole with a mass of M+1, 598.12 m/e. The product was redissolved in 100 ml of anhydrousacetonitrile by heating using a heat gun. To the reaction was added 11 mmol of thiomorpholine-1, 1-dioxide (TCIAmerica) and 1.1 mmol of 4-(dimethyl)aminopyridine. The reaction was stoppered and stirred for 12 hours. After 12hours, the reaction mixture was a slurry of crystals. The crystals were isolated by filtration through a medium sinteredglass funnel. The product was washed with cold acetonitrile and dried under vacuum. TLC analysis confirmed thatthe product was a single species giving 6.61 grams of product (99percent). ESI-Q-TOF mass spectroscopy analysisconfirmed the product as the 5?,3?-O-(tetraisopropyldisiloxane-1, 3-diyl)-2?-O-thiomorpholino-1, 1-dioxidethionocarbamatewith a mass of M+1, 664.21 m/e. Hydrogen fluoride-pyridine complex (HF:Py 7:3, 7 mL) was carefully toice-cold solution of pyridine (8 mL) in acetonitrile (46.5 mL). The pyridine-HF reagent so formed (32 mL) was thentransferred to the flask with 5?, 3?-O-(tetraisopropyldisiloxane-1,3-diyl)- 2?-O-thiomorpholino-1, 1-dioxidethionocarbamateprotected uridine (10 mmole), and the mixture was stirred at room temperature for 2 hours. The reactionwas quenched with 5percent solution of calcium chloride in water (300 mL). Crude product was extracted with EtOAc(3-5 times), and dried with anhydrous Na2SO4. After filtration organic layer was concentrated to a viscous oil giving3.4 grams (80percent yield) of product shown as a single spot by TLC with a confirmed identity of the 2?-O-thiomorpholino-1, 1-dioxidethionocarbamate protected uridine by ESI-Q-TOF mass spectroscopy with a mass of M+ 1, 422.10 m/e.2?-O-thiomorpholino-1, 1-dioxidethionocarbamate protected uridine (8.0 mmole) was redissolved in anhydrous THF(80 mL), 2,4,6-collidine (60 mmole) and dimethoxytrityl chloride (10.0 mmole) were added, and the mixture wasstirred at room temperature until TLC (CHCl3/MeOH 9:1) showed full disappearance of nucleoside substrate (16-24hours). 2,4,6-Collidine (8.0 mmole) and 1-methylimidazole (4.0 mmole) were added in one portion and N,N-diisopropylmethylphosphonamidicchloride (20 mmol) was added slowly to the reaction mixture over 10-15 minutes. Thereaction mixture was then stirred for another 2 hours. The solvent was removed in vacuo, and the crude productwas purified by column chromatography using hexanes with a gradient of EtOAc (0-50percent).
As the paragraph descriping shows that 39093-93-1 is playing an increasingly important role.
Reference£º
Patent; Agilent Technologies, Inc.; Dellinger, Douglas J.; Sierzchala, Agnieska; Turner, John; Myerson, Joel; Kupihar, Zoltan; Ferreira, Fernando; Caruthers, Marvin H.; EP2476689; (2015); B1;,
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