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Chemical Structure| 439118-13-5 Chemical Structure| 439118-13-5

Structure of 439118-13-5

Chemical Structure| 439118-13-5

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Product Details of [ 439118-13-5 ]

CAS No. :439118-13-5
Formula : C12H27NO2SSi
M.W : 277.50
SMILES Code : CC([S@@](N=CCO[Si](C)(C(C)(C)C)C)=O)(C)C

Safety of [ 439118-13-5 ]

Application In Synthesis of [ 439118-13-5 ]

* 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 [ 439118-13-5 ]

[ 439118-13-5 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 6086-21-1 ]
  • [ 439118-13-5 ]
  • S(S)-N-[(1S)-2-[tert-butyl(dimethyl)silyl]oxy-1-(2-methyl-1,2,4-triazol-3-yl)ethyl]-2-methyl-propane-2-sulfinamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% n-Butyl lithium (185 ml, 462 mmol) was added dropwise at ?78° C. under nitrogen to a solution of <strong>[6086-21-1]1-methyl-1H-[1,2,4]triazole</strong> (8 g, 96.43 mmol) in tetrahydrofuran (1000 mL), and the solution was stirred at this temperature for 30 minutes. A solution of [S(S)]-N-[2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethylidene]-2-methyl-2-propanesulfinamide (107 g, 385 mmol) Rech, J. C. et al. JACS (2007), 129(3), 490-491) in 1200 mL tetrahydrofuran was added dropwise at ?78° C. and stirred for 3 hours. The mixture was quenched with saturated aqueous NH4Cl (200 mL) and extracted with ethyl acetate (1000 ml×3). The combined organic layers were washed with saturated aqueous NaCl and dried over Na2SO4. Solids were filtered off, and the filtrate was concentrated to give crude material that was purified by silica gel column chromatography (gradient elution with petroleum ether/ethyl acetate from 20/1 to 3/1) to give the title compound (100 g, 72percent) as a yellow oil. 1H NMR (400 MHz, CDCl3) delta 0.00 (s, 3H), 0.04 (s, 3H), 0.85 (s, 3H), 1.3 (s, 9H), 4.0 (s, 3H), 4.2-4.6 (m, 2H), 4.7 (m, 1H), 7.9 (s, 1H).
  • 2
  • [ 6086-21-1 ]
  • [ 439118-13-5 ]
  • S(R)-N-[(1R)-2-[tert-butyl(dimethyl)silyl]oxy-1-(2-methyl-1,2,4-triazol-3-yl)ethyl]-2-methyl-propane-2-sulfinamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
55% An amount of n-butyl lithium (38.57 mL, 96.43 mmol) was added dropwise at ?78° C. under nitrogen to a solution of <strong>[6086-21-1]1-methyl-1H-[1,2,4]triazole</strong> (8 g, 96.43 mmol) in tetrahydrofuran (250 ml), and the solution was stirred at this temperature for 30 minutes. A solution of [S(R)]-N-[2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethylidene]-2-methyl-2-propanesulfinamide (22.3 g (80.36 mmol) (Seguin, C. et al. J. Org. Chem. (2009), 74(18), 6986-6992) in 20 mL tetrahydrofuran was added dropwise at ?78° C. and stirred for 3 hours. The mixture was quenched with saturated aqueous NH4Cl (40 ml). The above reaction was carried out again in a second batch. The two batches after the aqueous NH4Cl were combined and extracted with ethyl acetate (100 ml×3). The combined organic layers were washed with saturated aqueous NaCl and dried over Na2SO4. Solids were filtered off, and the filtrate was concentrated to give crude material that was purified by silica gel column chromatography (gradient elution with petroleum ether/ethyl acetate from 20/1 to 3/1) to give the title compound (31.8 g, 55percent) as a yellow oil. 1H NMR (400 MHz, CDCl3) delta 0.00 (s, 3H), 0.04 (s, 3H), 0.85 (s, 3H), 1.3 (s, 9H), 4.0 (s, 3H), 4.2-4.6 (m, 2H), 4.7 (m, 1H), 7.9 (s, 1H).
  • 3
  • [ 6086-21-1 ]
  • [ 439118-13-5 ]
  • S(S)-N-[(1S)-2-[tert-butyl(dimethyl)silyl]oxy-1-(2-methyl-1,2,4-triazol-3-yl)ethyl]-2-methyl-propane-2-sulfinamide [ No CAS ]
  • S(R)-N-[(1R)-2-[tert-butyl(dimethyl)silyl]oxy-1-(2-methyl-1,2,4-triazol-3-yl)ethyl]-2-methyl-propane-2-sulfinamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% 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).
 

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