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CAS No. : | 37002-45-2 | MDL No. : | MFCD00003212 |
Formula : | C21H26O8S2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | KPFDKWNWYAXRNJ-PMACEKPBSA-N |
M.W : | 470.56 | Pubchem ID : | 97439 |
Synonyms : |
|
Num. heavy atoms : | 31 |
Num. arom. heavy atoms : | 12 |
Fraction Csp3 : | 0.43 |
Num. rotatable bonds : | 8 |
Num. H-bond acceptors : | 8.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 113.19 |
TPSA : | 121.96 Ų |
GI absorption : | Low |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | Yes |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | Yes |
Log Kp (skin permeation) : | -6.87 cm/s |
Log Po/w (iLOGP) : | 4.22 |
Log Po/w (XLOGP3) : | 3.24 |
Log Po/w (WLOGP) : | 5.1 |
Log Po/w (MLOGP) : | 2.61 |
Log Po/w (SILICOS-IT) : | 2.39 |
Consensus Log Po/w : | 3.51 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -4.56 |
Solubility : | 0.013 mg/ml ; 0.0000277 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -5.47 |
Solubility : | 0.00158 mg/ml ; 0.00000335 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -6.3 |
Solubility : | 0.000237 mg/ml ; 0.000000505 mol/l |
Class : | Poorly soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 4.82 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
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 |
---|---|---|
60.7% | at 40 - 50℃; Inert atmosphere | A 250 mL 3 neck round bottom glass reactor equipped with a Teflon.(R). coated stir bar, a thermometer and its adapter, a reflux condenser with a gas inlet on top, and a Claisen adapter to which is attached a 60 mL addition funnel and a Teflon.(R). stopcock sample port is heated with a heat gun while purging with a rapid flow of N2 to degas. The reactor is then charged with 16.0 grams of (-)-1,4-di-O-tosyl-2,3-O-isopropylidene-L-threitol (CASNo. 37002-45-2, 36.1 mmol), aka bis(tosylate) and flushed with N2 purge for an additional 30 minutes. The bis(tosylate) is then dissolved in 100 mL of degassed, anhydrous THF. The sodium diarylphosphide solution prepared in Step 2). A). above is then transferred via cannula to the 60 mL addition funnel in parts and added dropwise to the rapidly stirring bis(tosylate) at rate so as to maintain a reactor temperature below 40° C. Upon addition to the electrophile, the reddish-orange color of the diarylphosphide salt rapidly disappears to give a final suspension with a beige color. After all of the phosphide is added, an oil bath is placed beneath the reactor and the contents heated to 50° C. for 45 minutes to complete phosphide coupling step. The Claisen adapter assembly is then replaced by a short path distillation head and roughly 50percent of the THF is removed. Then 100 mL of degassed heptane and water, each, are added to effect a phase split. The biphasic solution is then passed through an inerted glass fritted funnel to remove the carbon black and the lower aqueous phase removed via cannula. The upper organic phase is rinsed with an additional 50 mL of degassed water, again removed via cannula. The organic heptane phase is then extracted with 100 mL of anhydrous, degassed acetonitrile, the lower acetonitrile phase removed via cannula, and again the organic heptane phase is extracted with 50 mL of degassed acetonitrile. The acetonitrile phases are combined and transferred to a 1 neck round bottom flask with a Teflon.(R). stopcock on top with a 24/40 standard tapered ground glass joint on top. The volatiles are removed on a rotary evaporator to yield a viscous orange-brown glassy solid that is further dried under vacuum. In a dry box, the Teflon.(R). stopcock is replaced with a Claisen adapter to which is attached a reflux condenser with a gas inlet on top and a Teflon.(R). stopcock sample port. The glassy solid is then dissolved in crystallized in 100 mL of degassed methanol introduced by cannula or syringe followed by heating to reflux to completely dissolve the ligand. The heat is removed and the DIOP ligand suspension in the flask is immersed in an ice batch and cooled to -10° C. to yield a white to off-white/beige colored solid. The solid DIOP ligand is collected on a glass fritted Schlenck filter, rinsed with chilled methanol, and then dried overnight on the frit under vacuum. A total of 11.7 grams (23.5 mmol, 498.34 g/moll) of the (-)-DIOP ligand was isolated. The ligand is fully characterized by 1H(CDCl3: δ=7.58-7.29 ppm, cm, 20H, aromatic; δ=4.0-3.8 ppm, dd, 2H, -CH-; 6-2.50-2.25 ppm, ddd, 4H, -CH2-; δ1.35 ppm, s, 6H, -CH3) 13C (not reported here, but consistent with desired product), and 31P NMR (CDCl3: δ=-22.87 ppm, singlet, and a mol percent P purity>99percent) and by ICP for a total phosphorus content of 12.2 wt percent P (theory=12.4 wt percent P) representing a chemical purity of approximately 98.4percent for molecular formula=C31H32P2O2 and molecular weight=498.34 g/mol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With dmap; triethylamine; In dichloromethane; at 0 - 20℃; | To a solution of compound 4 (890 mg, 5.49 mmol) in TEA (2.29 mL, 16.5 mmol) and CH2Cl2 (50 mL) at 0 C were added tosyl chloride (2.62 g, 13.7 mmol) and a catalytic amount of 4-dimethylaminopyridine (DMAP). The reaction mixture was stirred overnight at room temperature. The reaction was quenched with water and the mixture extracted with CHCl3. The organic layer was washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. A silica gel mesh was prepared from the residue and submitted to flash chromatography (silica gel: EtOAc/hexane as eluent) to provide 12 (2.12 g, 82%). 1H-NMR (CDCl3, delta=7.26 ppm, 400 MHz,): 1.30 (s, 6H), 2.46 (s, 6H), 4.01 (m, 2H), 4.09 (m, 4H), 7.37 (m, 4H), 7.79 (m, 4H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With sodium azide; In N,N-dimethyl-formamide; at 80℃; for 18h; | To a solution of ((4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl)bis(methylene) bis(4- methylbenzenesulfonate) (5.23 g, 11.11 mmol) in DMF (20 mL) was added sodium azide (2.89 g, 44.5 mmol). The mixture was stirred at 80 C for 18 h. The mixture was diluted with water (100 mL) and extracted with EtOAc (2 x 100mL). The organic phase was washed with water (2 x 100 mL), brine (100 mL), dried with magnesium sulfate and concentrated to give (4S,5S)-4,5-bis(azidomethyl)-2,2-dimethyl-1,3-dioxolane (2.3 g, 10.8 mmol, 98% yield) as clear oil. 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 1.51 (s, 6 H), 3.30 - 3.43 (m, 2 H), 3.54 - 3.66 (m, 2 H), 4.10 (td, J=2.8, 1.3 Hz, 2 H). LCMS (m/z): no prominent [M + H]+. |
With sodium azide; In DMF (N,N-dimethyl-formamide); at 80℃; for 24h; | A mixture of (S,S),(-) 1,4-Di-O-p-toluolsulphonyl-2,3-O-isopropylidene-L-threitol (1.88 g, 4 mmol) and NaN3 (0.63 g, 10 mmol) in dmf (10 ml) was heated at 80C for 24 hrs. The dmf was removed in vacuo and the residue suspended in MTBE (150 ml). The organic layer was washed with water (3 x 100 ml), brine (100 ml), dried over MgSO4, filtered and the solvent removed by rotary evaporation to give the crude diazide. The product was obtained by column chromatography on silica gel, eluting with hexane : EtOAC (9 : 1) to give the pure diazide as a colourless liquid. 1H NMR (CDCl3, 400 MHz) delta 3.90 (1H, CH), 3.30 (2H, dddd, CH2). 1.3 (3H, s, CH3) ; 13C NMR (CDCl3, 100 MHz) delta 110 (C), 76.6 (CH), 51.6 (CH2), 26. 8 (CH3). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In N-methyl-acetamide; ice-water; | A. 2.92 g of methyl 4'-hydroxy-biphenyl-4-carboxylate and 1.77 g of finely ground potassium carbonate suspended in 25 ml of dimethylformamide were treated with 2,0 g of 2,3-O-isopropylidene-1,4-bis-O-(4-methyl-phenylsulfonyl)-L-threitol. The reaction mixture was stirred at 130 C. under argon for 18 hours. The reaction solution was subsequently poured on to ice-water and the separated precipitate was filtered off and chromatographed on silica gel with methylene chloride/methanol. There was thus obtained 2,3-O-isopropylidene-1,4-bis-O-(4'-methoxycarbonyl-biphenyl-4-yl)-L-threitol as a colorless solid, MS: m/z 582 ([M]+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In N-methyl-acetamide; dichloromethane; | C. 0.71 g of 2,3-O-isopropylidene-1,4-bis-O-(4-methyl-phenylsulfonyl)-L-threitol, 1.0 g of methyl 4-[2-(4-hydroxy-phenyl)-ethyl]-benzoate and 0.54 g of finely ground anhydrous potassium carbonate were suspended in 20 ml of dimethylformamide and stirred at 130 C. under argon for 18 hours. Subsequently, the reaction mixture was diluted with water and extracted with ethyl acetate. The combined ethyl acetate phases were dried over magnesium sulfate and concentrated. The residue was chromatographed on silica gel with 5% ether in methylene chloride. There was thus obtained 2,3-O-isopropylidene-1,4-bis-O-[4-[2-(4-methoxycarbonyl-phenyl)-ethyl]-phenyl]-L-threitol in the form of colorless crystals, MS: m/z 638 ([M]+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In dichloromethane; acetonitrile; | B. 6.0 g of 2,3-O-isopropylidene-1,4-di-O-(4-methyl-phenyl-sulfonyl)-L-threitol, 2.13 g of methyl 4-hydroxybenzoate and 1.94 g of finely ground anhydrous potassium carbonate were suspended in 100 ml of acetonitrile and stirred at 100 C. under argon for 18 hours. Subsequently, the reaction mixture was diluted with water, extracted with methylene chloride and the combined methylene chloride phases were dried over magnesium sulfate and concentrated. The residue was chromatographed on silica gel with 5% ether in methylene chloride. There was thus obtained 2,3-O-isopropylidene-1-O-(4-methoxycarbonyl-phenyl)-4-O-(4-methyl-phenylsulfonyl)-L-threitol as a colorless oil, MS: m/z 450 ([M]+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In dichloromethane; acetonitrile; | A. 37.6 g of 2,3-O-isopropylidene-1,4-di-O-(4-methyl-phenyl-sulfonyl)-L-threitol, 16.0 g of methyl 3-hydroxy-naphthalene-2-carboxylate and 13 g of finely ground anhydrous potassium carbonate were suspended in 300 ml of acetonitrile and stirred at 100 C. under argon for 60 hours. Subsequently, the reaction mixture was diluted with water and the aqueous phase was extracted with ether. The combined ether phases were dried over magnesium sulfate and concentrated. The thus-obtained crude product was chromatographed on silica gel with ether in methylene chloride. There was thus obtained crude 2,3-O-isopropylidene-1-O-(3-methoxycarbonyl-naphthalen-2-yl)-4-O-(4-methyl-phenylsulfonyl)-L-threitol. | |
With potassium carbonate; In dichloromethane; acetonitrile; | C. 3.76 g of 2,3-O-isopropylidene-1,4-bis-O-(4-methyl-phenylsulfonyl)-L-threitol, 1.60 g of methyl 3-hydroxy-naphthalene-2-carboxylate and 1.3 g of finely ground anhydrous potassium carbonate were suspended in 50 ml of acetonitrile and stirred under reflux and under argon for 60 hours. The reaction mixture was subsequently diluted with water and extracted with methylene chloride. The combined methylene chloride phases were dried over magnesium sulfate, concentrated and the residue was chromatographed on silica gel with 5% ether in methylene chloride. There was thus obtained 2,3-O-isopropylidene-1-O-(3-methoxycarbonyl-naphthalen-2-yl)-4-O-(4-methyl-phenylsulfonyl)-L-threitol as a colorless oil, MS: m/z 500 ([M]+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In N-methyl-acetamide; | A. 9.5 g of 2,3-O-isopropylidene-1,4-bis-O-(4-methyl-phenyl-sulfonyl)-L-threitol and 5.86 g of 4-(4-benzyloxy-benzyl)-phenol (Example 51.A.) were reacted at 100 C. for 6 hours in 300 ml of dimethylformamide with the addition of 27.9 g of potassium carbonate. The reaction mixture was subsequently worked up extractively with ice-water and methylene chloride. The crude product was chromatographed on silica gel with n-hexane/ethyl acetate. There was thus obtained 1-O-[4-(4-benzyloxy-benzyl)-phenyl]-2,3-O-isopropylidene-4-O-(4-methyl-phenylsulfonyl)-L-threitol as a colorless oil, MS: m/z 588.0 ([M]+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
The acetonide is reduced with LiAlH4 to the corresponding diol acetonide which is reacted with toluene-sulfonyl chloride to give 1,4-ditosyl-2,3-O-isopropylidene-L-threitol. Reaction of this with sodium diphenylphosphide gives the desired ligand. STR8 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
To an ethanol (100 mL) suspension of 1,4 di-O-tosyl-2,3-O-isopropylidene-L-threitol (10.0 g, 21.25 mmol), p-toluenesulfonic acid monohydrate (0.40 g) was added, and the mixture was heated to reflux for 4 days with stirring. The reaction liquor was cooled, and then the solvent was concentrated under reduced pressure. A saturated aqueous solution of sodium hydrogen carbonate (50 mL) was added to the obtained residue, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure, to obtain the title compound as a solid. This compound was used in the subsequent reaction without performing further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60.7% | In tetrahydrofuran; Carnea E-22; at 40 - 50℃;Inert atmosphere;Product distribution / selectivity; | A 250 mL 3 neck round bottom glass reactor equipped with a Teflon coated stir bar, a thermometer and its adapter, a reflux condenser with a gas inlet on top, and a Claisen adapter to which is attached a 60 mL addition funnel and a Teflon stopcock sample port is heated with a heat gun while purging with a rapid flow of N2 to degas. The reactor is then charged with 16.0 grams of (-)-1,4-di-O-tosyl-2,3-O-isopropylidene-L-threitol (CASNo. 37002-45-2, 36.1 mmol), aka bis(tosylate) and flushed with N2 purge for an additional 30 minutes. The bis(tosylate) is then dissolved in 100 mL of degassed, anhydrous THF. The sodium diarylphosphide solution prepared in Step 2). A). above is then transferred via cannula to the 60 mL addition funnel in parts and added dropwise to the rapidly stirring bis(tosylate) at rate so as to maintain a reactor temperature below 40 C. Upon addition to the electrophile, the reddish-orange color of the diarylphosphide salt rapidly disappears to give a final suspension with a beige color. After all of the phosphide is added, an oil bath is placed beneath the reactor and the contents heated to 50 C. for 45 minutes to complete phosphide coupling step. The Claisen adapter assembly is then replaced by a short path distillation head and roughly 50% of the THF is removed. Then 100 mL of degassed heptane and water, each, are added to effect a phase split. The biphasic solution is then passed through an inerted glass fritted funnel to remove the carbon black and the lower aqueous phase removed via cannula. The upper organic phase is rinsed with an additional 50 mL of degassed water, again removed via cannula. The organic heptane phase is then extracted with 100 mL of anhydrous, degassed acetonitrile, the lower acetonitrile phase removed via cannula, and again the organic heptane phase is extracted with 50 mL of degassed acetonitrile. The acetonitrile phases are combined and transferred to a 1 neck round bottom flask with a Teflon stopcock on top with a 24/40 standard tapered ground glass joint on top. The volatiles are removed on a rotary evaporator to yield a viscous orange-brown glassy solid that is further dried under vacuum. In a dry box, the Teflon stopcock is replaced with a Claisen adapter to which is attached a reflux condenser with a gas inlet on top and a Teflon stopcock sample port. The glassy solid is then dissolved in crystallized in 100 mL of degassed methanol introduced by cannula or syringe followed by heating to reflux to completely dissolve the ligand. The heat is removed and the DIOP ligand suspension in the flask is immersed in an ice batch and cooled to -10 C. to yield a white to off-white/beige colored solid. The solid DIOP ligand is collected on a glass fritted Schlenck filter, rinsed with chilled methanol, and then dried overnight on the frit under vacuum. A total of 11.7 grams (23.5 mmol, 498.34 g/moll) of the (-)-DIOP ligand was isolated. The ligand is fully characterized by 1H(CDCl3: delta=7.58-7.29 ppm, cm, 20H, aromatic; delta=4.0-3.8 ppm, dd, 2H, -CH-; 6-2.50-2.25 ppm, ddd, 4H, -CH2-; delta1.35 ppm, s, 6H, -CH3) 13C (not reported here, but consistent with desired product), and 31P NMR (CDCl3: delta=-22.87 ppm, singlet, and a mol % P purity>99%) and by ICP for a total phosphorus content of 12.2 wt % P (theory=12.4 wt % P) representing a chemical purity of approximately 98.4% for molecular formula=C31H32P2O2 and molecular weight=498.34 g/mol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
33% | With potassium carbonate; In N,N-dimethyl-formamide; at 100℃; for 2h;Microwave irradiation; | Example 57di-ferf-butyl (4S)-N-(tert-butoxYcarbonYl)^-(4-{r(4S15S)-212-dimethYl-5-({r(4- methvlphenvl)sulfonvlloxv)methvl)-1 ,3-dioxolan-4-vllmethoxv>benzyl)-L- glutamate; To 0.47 g (1 mmol) (4S)-/V-(fert-butoxycarbonyl)-4-(4-hydroxybenzyl)-L-glutamate and 0.47 g (1 mmol) [(4S,5S)-2.2-dimethyl-1 ,3-dioxolane-4.5-diyl]dimethanediyl bis(4- methylbenzenesulfonate) in 15 mL DMF was added potassium carbonate (0.28 g, 2 mmol). The mixture was heated in a microwave for 2 h at 100 C. Water was added and the mixture was extracted with dichloromethane. The organic phase was dried over sodium sulfate, filtered and concentrated. The crude product was purified by flash chromatography (silica, 20% ethyl acetate in hexane) to afford 0.25 g (33%) di-fert-butyl (4S)-N-(tert-butoxycarbonyl)-4-(4-[(4S.5S)-2,2-dimethyl-5-([(4- methylphenyl)sulfonyl]oxy}methyl)-1 ,3-dioxolan-4-yl]methoxy}benzyl)-L-glutamate.1H-NMR (400MHz, CHLOROFORM-d): delta [ppm]= 1 .31 (s, 9H), 1 .37 - 1 .53 (m, 23H), 1.87 (t, 2H), 2.44 (s, 3H), 2.61 (quin, 1 H), 2.81 (br. d, 2H), 3.92 - 3.97 (m, 1 H), 4.06 - 4.29 (m, 7H), 4.88 (d, 1 H), 6.74 (d, 2H), 7.08 (d, 2H), 7.33 (d, 2H), 7.80 (d, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | With potassium carbonate; In N,N-dimethyl-formamide; at 100℃; for 2h; | Example 53di-ferf-butyl (2S)-2-r(tert-butoxYcarbonYl)amino1-5-(4-{r(4S,5S)-2,2-climethYl-5-({r(4- methvlphenvl)sulfonylloxv)methvH-1 ,3-dioxolan-4- vnmethoxv)benzyl)hexanedioate; 500 mg (1 .04 mmol) (2S)-2-fert.-Butoxycarbonylamino-5-(4-hydroxy-benzyl - hexanedioic acid di-fert. -butyl ester, 144 mg (1 .04 mmol) potassium carbonate and 491 mg (1.04 mmol) [(4S.5S)-2,2-dimethyl-1 ,3-dioxolane-4,5-diyl]bis(methylene) bis(4- methylbenzenesulfonate) in 12 mL DMF were heated in a microwave at 100 C for 2 h. Brine (300 mL) was added and the mixture was extracted with dichloromethane (3 x 100 mL). The combined organic fractions were dried over sodium sulfate and concentracted. The crude product was purified by Flash chromatography (Silica, 2-40% ethyl acetate in hexane) to afford 430 mg (52%) di-fert-butyl (2S)-2-[(tert- butoxycarbonyl)amino]-5-(4-[(4S,5S)-2,2-dimethyl-5-([(4- methylphenyl)sulfonyl]oxy}methyl)-1.3-dioxolan-4-yl]methoxy}benzyl)hexanedioate. 1H-NMR (400 MHz, CHLOROFORM-d): delta [ppm]= 1 .32-1 .68 (m, 19H), 1 .71-1 .85 (m, 1 H), 2.44 (s, 3H). 2.46-2.66 (m, 2H), 2.78-2.87 (m, 1 H). 3.94 (dd, 1 H), 4.06-4.29 (m, 6H), 5.03 (br. s, 1 H), 6.74 (d, 2H). 7.06 (dd. 2H), 7.33 (d, 2H), 7.80 (d, 2H).ES+ m/z 778 (M+H), 800 (M+Na). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | In toluene;Reflux; | 1-Butylimidazole (0.37 g, 3.0 mmol) was added dropwisely to a solution of 2811 (0.50 g, 1.0 mmol) in toluene (5 mL). The mixture was stirred at reflux temperature overnight. The crude product was washed with toluene, and the remaining solvent was evaporated in vacuo to give 30 (0.72 g, quant.) as a brown amorphous solid; 1H NMR (500 MHz, CDCl3) delta: 0.85 (6H, t, J=7.3 Hz, CH3CH2CH2CH2), 1.23 (4H, sext, J=7.3 Hz, CH3CH2CH2CH2), 1.31 (6H, s, CH3), 1.72 (4H, quint, J=7.3 Hz, CH3CH2CH2CH2), 2.32 (6H, s, tosyl), 4.11 (4H, m, CH3CH2CH2CH2), 4.26 (2H, dt, J=14.3, 2.3 Hz, CH), 4.62 (2H, dd, J=14.3, 2.3 Hz, CH2), 4.94 (2H, d, J=14.3Hz, CH2), 7.24 (2H, s, imidazole), 7.63 (2H, s, 8.0Hz, imidazole), 9.64 (2H, s, imidazole); 13C NMR (126 MHz, CDCl3) delta: 13.4, 19.5, 21.4, 27.0, 31.9, 49.9, 50.3, 75.9, 111.4, 121.6, 123.9, 125.9, 128.8, 137.8, 139.5, 143.6; IR (neat) cm-1: 1564, 1456, 1186, 1119, 1032, 1011; HRMS (FAB) m/z: [MTsO]+, found 547.2964. C28H43N4O5S requires 547.2943; MS (FAB-) m/z: 171; [alpha]D22 -27.03 (c 0.3, CH3OH). |
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P337 | If eye irritation persists: |
P338 | Remove contact lenses, if present and easy to do. Continue rinsing. |
P340 | Remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P341 | If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P342 | If experiencing respiratory symptoms: |
P350 | Gently wash with plenty of soap and water. |
P351 | Rinse cautiously with water for several minutes. |
P352 | Wash with plenty of soap and water. |
P353 | Rinse skin with water/shower. |
P360 | Rinse immediately contaminated clothing and skin with plenty of water before removing clothes. |
P361 | Remove/Take off immediately all contaminated clothing. |
P362 | Take off contaminated clothing and wash before reuse. |
P363 | Wash contaminated clothing before reuse. |
P370 | In case of fire: |
P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
P373 | DO NOT fight fire when fire reaches explosives. |
P374 | Fight fire with normal precautions from a reasonable distance. |
P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
P377 | Leaking gas fire: Do not extinguish, unless leak can be stopped safely. |
P378 | |
P380 | Evacuate area. |
P381 | Eliminate all ignition sources if safe to do so. |
P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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