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[ CAS No. 133384-73-3 ] {[proInfo.proName]}

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Chemical Structure| 133384-73-3
Chemical Structure| 133384-73-3
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Product Details of [ 133384-73-3 ]

CAS No. :133384-73-3 MDL No. :
Formula : C14H20O5S Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 300.37 Pubchem ID :-
Synonyms :

Safety of [ 133384-73-3 ]

Signal Word: Class:
Precautionary Statements: UN#:
Hazard Statements: Packing Group:

Application In Synthesis of [ 133384-73-3 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 133384-73-3 ]

[ 133384-73-3 ] Synthesis Path-Downstream   1~7

  • 1
  • [ 4728-12-5 ]
  • [ 98-59-9 ]
  • [ 133384-73-3 ]
YieldReaction ConditionsOperation in experiment
97% With triethylamine; In dichloromethane; at 0 - 20℃; for 1h; 30.1.(2,2-dimethyl-1,3-dioxan-5-yl)methyl 4-methylbenzenesulfonateTo a solution of 1.5 g (10.26 mmol) of (2,2-dimethyl-1,3-dioxan-5-yl)methanol and 1.71 mL of Et3N in 15 mL of DCM, cooled to 0° C., are added 2.15 g (11.3 mmol) of tosyl chloride.The medium is allowed to warm to room temperature, and stirring is continued for 1 hour.The medium is taken up in 100 mL of DCM, washed successively with 0.1N HCl (2*20 mL) and brine (20 mL), dried over Na2SO4, concentrated under reduced pressure and then purified by chromatography on a column of silica gel, eluting with a 99/1 DCM/MeOH mixture.3 g of (2,2-dimethyl-1,3-dioxan-5-yl)methyl 4-methylbenzenesulfonate are obtained in the form of a colourless oil.Yield=97percent1H NMR, CDCl3, 400 MHz, delta (ppm): 7.8 (d, 2H); 7.3 (d, 2H); 4.1 (d, 2H); 3.9 (dd, 2H); 3.6 (dd, 2H); 2.4 (s, 3H); 1.9 (m, 1H); 1.4 (s, 3H); 1.2 (s, 3H)
68.8% With 1,4-diaza-bicyclo[2.2.2]octane; In dichloromethane; for 0.25h;Cooling with ice; To a dried 50 mL round bottom flask were added compound Ii?-1 (470 mg, 3.22 mmol), DABCO (721.9 mg, 6.43 mmol) and CH2Cl2 (15 mL). With an ice bath, TsCl (675.3 mg, 3.54 mmol) was added slowly to the solution. After the solution was stirred for 15 minutes, TLC showed the disappearance of the raw materials. The mixture was diluted with CH2Cl2 (20 mL) when the reaction finished, and after filtration, the filtrate was washed in turn with hydrochloric acid (1 N, 15 mL), saturated aqueous sodium bicarbonate (15 mL) and saturated brine (15 mL). The organic phase was dried over anhydrous sodium sulfate, the solvent was evaporated under vacuum to give compound Ih?-1 (665 mg, 68.8percent). [0140] LC-MS (ESI): m/z=301 [M+H]+, 323 [M+Na]+.
68.8% With 1,4-diaza-bicyclo[2.2.2]octane; In dichloromethane; for 0.25h;Cooling with ice; Example 8: Preparation of Compound Ih"-1: [0095] To a dried 50 mL round bottom flask were added compound Ii"-1 (470 mg, 3.22 mmol), DABCO (721.9 mg,6.43 mmol) and CH2Cl2 (15 mL). With an ice bath, TsCl (675.3mg, 3.54mmol) was added slowly to the solution. Afterthe solution was stirred for 15 minutes, TLC showed the disappearance of the raw materials. The mixture was dilutedwith CH2Cl2 (20 mL) when the reaction finished, and after filtration, the filtrate was washed in turn with hydrochloric acid(1 N, 15 mL), saturated aqueous sodium bicarbonate (15 mL) and saturated brine (15 mL). The organic phase wasdried over anhydrous sodium sulfate, the solvent was evaporated under vacuum to give compound Ih"-1 (665 mg, 68.8percent).LC-MS (ESI): m/z = 301 [M+H]+,323 [M+Na]+.
With dmap; triethylamine; In dichloromethane; at 0 - 20℃; A solution of (2,2-dimethyl-1 ,3-dioxan-5-yl)methanol (2.51 g, 17.1 mmol) and N, N- dimethylaminopyiridine (208 mg, 1.7 mmol) in dichloromethane (100 ml.) was cooled to 0 0C and p-toluenesulfonyl chloride (3.59 g, 18.8 mmol) and triethylamine (4.8 ml. 34.2 mmol) were added. The mixture was stirred overnight at rt, diluted with water, and the organic layer was separated. The solvent was removed and the crude material was purified via silica gel chromatography to give 4.16 g of the title compound. 1H NMR (DMSOd6) delta 7.78 (d, 2 H), 7.47 (d, 2 H), 4.09 (d, 2 H), 3.84 (dd, 2 H), 3.52 (dd, 2 H), 2.41 (s, 3 H), 1.79 - 1.94 (m, 1 H), 1.28 (s, 3 H), 1.18 (s, 3 H).

Reference： [1]Patent: US2011/294788,2011,A1 .Location in patent: Page/Page column 32
[2]Tetrahedron,1991,vol. 47,p. 1001 - 1012
[3]Patent: US2013/324464,2013,A1 .Location in patent: Paragraph 0139; 0140
[4]Patent: EP2676965,2013,A1 .Location in patent: Paragraph 0093; 0095
[5]Chemical and Pharmaceutical Bulletin,1993,vol. 41,p. 339 - 345
[6]European Journal of Organic Chemistry,2006,p. 719 - 728
[7]Patent: WO2008/157330,2008,A1 .Location in patent: Page/Page column 68
  • 2
  • [ 133384-73-3 ]
  • [ 5413-80-9 ]
  • [ 135488-42-5 ]
YieldReaction ConditionsOperation in experiment
40% With sodium hydride
Reference： [1]Gatta; Gradoni; Lupardini; Gramiccia; Orsini [Il Farmaco, 1991, vol. 46, # 1, p. 75 - 84]
  • 3
  • [ 51335-75-2 ]
  • [ 133384-73-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 74 percent / aq. NaCl / dimethylsulfoxide / 24 h / 180 °C 2: LiAlH4 / diethyl ether / 5 h / Ambient temperature 3: pyridine / 3 h / Ambient temperature
Multi-step reaction with 3 steps 1: 65 percent / NaCl / H2O; dimethylsulfoxide / 6 h / Heating 2: 99 percent / LiAlH4 / diethyl ether / 2.5 h / Ambient temperature 3: 93 percent / pyridine / 2.5 h / 0 °C
Reference： [1]Iwata; Maezaki; Hattori; Fujita; Moritani; Takemoto; Tanaka; Imanishi [Chemical and Pharmaceutical Bulletin, 1993, vol. 41, # 2, p. 339 - 345]
[2]Dubois, Joelle; Foures, Christine; Bory, Sonia; Falcou, Serge; Gaudry, Michel; Marquet, Andree [Tetrahedron, 1991, vol. 47, # 6, p. 1001 - 1012]
  • 4
  • [ 82962-54-7 ]
  • [ 133384-73-3 ]
Reference： [1]Chemical and Pharmaceutical Bulletin,1993,vol. 41,p. 339 - 345
[2]Tetrahedron,1991,vol. 47,p. 1001 - 1012
[3]Patent: US2013/324464,2013,A1
[4]Patent: EP2676965,2013,A1
  • 5
  • [ 107516-75-6 ]
  • [ 133384-73-3 ]
  • C21H27NO6 [ No CAS ]
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 1994 - 1999
  • 6
  • [ 4728-12-5 ]
  • [ 104-15-4 ]
  • [ 133384-73-3 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In dichloromethane; at 20℃; for 4h; To a solution of (2,2-dimethyl-l,3-dioxan-5-yl)methanol (1.078 g) in dichloromethane (20 mL) were added TEA (2.056 mL) and para-toluenesulfonyl chloride (1.687 g). The reaction mixture was stirred at room temperature for 4 hours and concentrated. The concentrate was partitioned between water and ethyl acetate. The organic <n="86"/>layer was washed with brine, dried over Na2SO4, filtered and concentrated. The cruconcentrate was purified by flash chromatography (Analogix SF25chi40g with 10percent ethyl acetate/hexanes). MS (ESI) m/z 301.1 (M+l)+, 318.2 (M+18)+.
Reference： [1]Patent: WO2009/129385,2009,A1 .Location in patent: Page/Page column 84-85
  • 7
  • [ 133384-73-3 ]
  • [ 4983-28-2 ]
  • 2-chloro-5-[(2,2-dimethyl-1,3-dioxan-5-yl)methoxy]pyrimidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% With caesium carbonate; In 1-methyl-pyrrolidin-2-one; at 70℃; for 3.5h; (Reference Example 20) 2-Chloro-5-[(2,2-dimethyl-1,3-dioxan-5-yl)methoxy]pyrimidine To 2.53 g (19.4 mmol) of <strong>[4983-28-2]2-chloro-5-hydroxypyrimidine</strong>, a solution of 5.95 g (19.8 mmol) of 5-(toluenesulfonyloxymethyl)-2,2-dimethyl-1,3-dioxane in 11 ml of N-methylpyrrolidone and 6.50 g (19.9 mmol) of cesium carbonate were added, and the reaction mixture was stirred at 70°C for 3.5 hours. After completion of the reaction, the reaction solution was poured into water and extracted with ethyl acetate twice. The obtained organic layers were combined, washed with water and saturated sodium chloride aqueous solution in order and dried with anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. tert-Butyl methyl ether was added to the obtained residue, and the precipitate was obtained by filtration to provide 3.72 g of the title compound as a white solid (yield: 74percent). 1H-NMR spectrum (300 MHz, CD2 Cl2) delta: 8.31 (2H, s), 4.22 (2H, d, J = 7.1 Hz), 4.11 (2H, dd, J = 12.5, 3.7 Hz), 3.82 (2H, dd, J = 12.5, 4.2 Hz), 2.05 (1H, ttt, J = 7.5, 3.8, 3.8 Hz), 1.44 (3H, s), 1.36 (3H, s). Mass spectrum (CI, m/z): 259 [M+ +1].
Reference： [1]Patent: EP2801574,2014,A1 .Location in patent: Paragraph 0267; 0268

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