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CAS No. : | 1519-39-7 | MDL No. : | MFCD00151502 |
Formula : | C8H10OS | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | FEVALTJSQBFLEU-SNVBAGLBSA-N |
M.W : | 154.23 | Pubchem ID : | 10913262 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P280-P305+P351+P338-P304+P340 | UN#: | |
Hazard Statements: | H302 | Packing Group: | |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With lithium diisopropyl amide In tetrahydrofuran 1.) -0 deg C, 30 min, 2.) 0 deg C, 2 h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With lithium diisopropyl amide In tetrahydrofuran at -78℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With lithium diisopropyl amide In tetrahydrofuran at -78.15℃; for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | Stage #1: (R)-methyl p-tolyl sulfoxide With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1.5h; Stage #2: (S)-N-(tert-butoxycarbonyl)alanine methyl ester In tetrahydrofuran at -25℃; for 3.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | Stage #1: (R)-methyl p-tolyl sulfoxide With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1h; Stage #2: (S)-N-(tert-butoxycarbonyl)proline methyl ester In tetrahydrofuran at -78℃; for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With lithium diisopropyl amide In tetrahydrofuran; hexane at -78 - 0℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | Stage #1: (R)-methyl p-tolyl sulfoxide With lithium diisopropyl amide In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: N-(4-methoxybenzylidene)aniline In tetrahydrofuran; hexane at -78℃; for 0.166667h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 94% 2: 2% | With cesium fluoride In tetrahydrofuran Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | Stage #1: (R)-methyl p-tolyl sulfoxide With lithium diisopropyl amide In tetrahydrofuran at -78℃; Stage #2: (2E,4E)-ethyl hexa-2,4-dienoate In tetrahydrofuran for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | Stage #1: (R)-methyl p-tolyl sulfoxide With lithium diisopropyl amide In tetrahydrofuran; hexane at -40℃; for 1h; Inert atmosphere; Stage #2: C6H4(CH2CH2C(O)O) In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | Stage #1: (R)-methyl p-tolyl sulfoxide With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 2h; Inert atmosphere; Stage #2: (S)-N-(tert-butoxycarbonyl)alanine methyl ester In tetrahydrofuran at -25℃; for 12h; Inert atmosphere; optical yield given as %de; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | Stage #1: (R)-methyl p-tolyl sulfoxide With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 2h; Inert atmosphere; Stage #2: (S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester In tetrahydrofuran at -25℃; for 12h; Inert atmosphere; optical yield given as %de; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57% | Stage #1: (R)-methyl p-tolyl sulfoxide With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 2h; Inert atmosphere; Stage #2: N-tert-butoxycarbonyl-L-valine methyl ester In tetrahydrofuran at -25℃; for 12h; Inert atmosphere; optical yield given as %de; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | Stage #1: (R)-methyl p-tolyl sulfoxide With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 2h; Inert atmosphere; Stage #2: N-tert-butoxycarbonyl-L-leucine methyl ester In tetrahydrofuran at -25℃; for 12h; Inert atmosphere; optical yield given as %de; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 70% 2: 20% | Stage #1: (R)-methyl p-tolyl sulfoxide With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.166667h; Inert atmosphere; Stage #2: 6-methyl-2-oxo-1,2-dihydropyrimidine-5-carboxylic acid ethyl ester In tetrahydrofuran at -78 - 20℃; Inert atmosphere; chemoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | Stage #1: (R)-methyl p-tolyl sulfoxide With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: ethyl-2-picolinate In hexane; ethyl acetate at -78℃; for 0.5h; Inert atmosphere; | 1. Chemistry. Synthesis of -ketosulfoxides. General Procedure General procedure: A freshly prepared solution of LDA (6.46 mmol, 2 eq.) in THF fromdiisopropylamine (7.11 mmol, 2.2 eq.) in THF (10 mL) at -78 °C and 2 M de nBuLi solution in hexane (3.23 mL, 6.46 mmol, 2 eq.), is added over the corresponding methyl sulfoxide (3.23 mmol, 1 eq.) in THF (10 mL), at -78°C, under argon. After stirring for 30 min. the formed carbanion solution is added over a THF solution (10 mL) of the corresponding ethyl carboxylate (3.23 mmol, 1 eq.), at -78°C, under argon. After stirring for 30 min., the reaction mixture was quenched with saturated NH4Cl, aqueous solution and 1M H2SO4 was added until pH 3-4. The aqueous phase was then extracted with EtOAc (5 x 50 mL), washed with saturated NaHCO3 aqueous solution and saturated NaCl aqueous solution, and dried over Na2SO4. After removing the solvent at vacuo, the residue was purified by flash chromatography, to give the corresponding -ketosulfoxide. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | Stage #1: (R)-methyl p-tolyl sulfoxide With lithium dipropan-2-ylazanide In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: 3,5-dimethoxybenzoic acid methyl ester In tetrahydrofuran; hexane at -78℃; for 2h; Inert atmosphere; |