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Chemical Structure| 342651-75-6 Chemical Structure| 342651-75-6

Structure of 342651-75-6

Chemical Structure| 342651-75-6

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Product Details of [ 342651-75-6 ]

CAS No. :342651-75-6
Formula : C12H27NO2SSi
M.W : 277.50
SMILES Code : CC([S@](N=CCO[Si](C)(C(C)(C)C)C)=O)(C)C

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Application In Synthesis of [ 342651-75-6 ]

* 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 [ 342651-75-6 ]

[ 342651-75-6 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 6086-21-1 ]
  • [ 342651-75-6 ]
  • (R)-N-[(R)-2-(tert-butyldimethylsilyloxy)-1-(1-methyl-1H-1,2,4-triazol-5-yl)ethyl]-2-methylpropane-2-sulfinamide [ No CAS ]
  • C15H32N4O2SSi [ No CAS ]
YieldReaction ConditionsOperation in experiment
55% General procedure: To a solution of <strong>[6086-21-1]1-methyl-1H-[1,2,4]triazole</strong> (38.4 g, 462 mmol) in THF (1.2 L) at ?78 °C under N2 atmosphere was added a solution of n-BuLi (185 mL, 2.5 M, 462.5 mmol) in hexane dropwise at ?78 °C with stirring over 2 h. After the addition, the mixture was stirred at this temperature for 30 min. A solution of (SS)-4 (106.8 g, 385 mmol) in THF (1.2 L) was added dropwise to the mixture, and stirred for 3 h until TLC (PE?EtOAc, 2:1) showed the reaction was complete. The solution was quenched with sat. aq NH4Cl (1 L) at r.t. and extracted with EtOAc (3 × 0.5 L), and the combined organic layers were washed with brine (1 L) and concentrated. The crude product was purified by chromatography on silica gel (eluent: PE?EtOAc, 20:1 ? 3:1) to give the title compound; yield: 99.8 g (72percent); yellow oil; Rf = 0.3 (EtOAc?PE, 1:5).
  • 2
  • [ 342651-75-6 ]
  • [ 30506-30-0 ]
  • (R)-N-((R)-2-((tert-butyldimethylsilyl)oxy)-1-(4-(ethylthio)phenyl)ethyl)-2-methylpropane-2-sulfinamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
(0208) (0209) At -65 C, n-BuLi (2.5 M, 63.42 mL, 2.20 eq) was added dropwise to a solution of Compound 10-1-F (31.30 g, 144.14 mmol, 2.00 eq) in 150 mL anhydrous tetrahydrofuran. After the completion of the dropwise addition, the reaction solution was stirred at the same temperature for half an hour. A solution of Compound 10-1-E (20.00 g, 72.07 mmol, 1.00 eq) in 50 mL anhydrous tetrahydrofuran was added dropwise to the reaction solution at -65 C. Upon the completion of the dropwise addition, the reaction solution was stirred at the same temperature for 2 hours, and then heated to 30 C and stirred for 2 hours. LC-MS showed that Compound 10-1-E was completely consumed and there was a main peak showing the MS of the product. The reaction solution was quenched with 200 mL saturated ammonium chloride solution and then extracted twice with 200 mL ethyl acetate. The combined organic phases were washed sequentially with 200 mL of water and saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated to give a crude product. The crude product was purified by a flash column (ISCO; SepaFlash silica gel flash column (120g), eluent: ethyl acetate and petroleum ether; elution gradient: 0% to 20%; flow rate: 80 mL/min) to obtain Compound 10-1-G. MS (ESI) m/z: 438.2 [M+Na]+; 1H NMR (400 MHz, CHLOROFORM-d) δ = 7.15 - 7.23 (m, 4 H), 4.42 (m, 1 H), 4.19 (s, 1 H), 3.67 - 3.71 (m, 1 H), 3.49 - 3.55 (m, 1 H), 2.88 (q, J=7.4 Hz, 2 H), 1.25 (t, J=7.4 Hz, 3 H), 1.14 - 1.17 (m, 9 H), 0.83 (s, 9 H), -0.01 (d, J=7.6 Hz, 6 H).
 

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