[ CAS No. 25554-84-1 ] {[proInfo.proName]}

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Quality Control of [ 25554-84-1 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 25554-84-1 ]

Product Details of [ 25554-84-1 ]

CAS No. :	25554-84-1	MDL No. :	MFCD00022145
Formula :	C₅H₈O₃S₂	Boiling Point :	-
Linear Structure Formula :	(C₂H₅O)(HOOCCH₂S)CS	InChI Key :	-
M.W :	180.25	Pubchem ID :	-
Synonyms :

Safety of [ 25554-84-1 ]

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Application In Synthesis of [ 25554-84-1 ]

* 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.

Upstream synthesis route of [ 25554-84-1 ]
Downstream synthetic route of [ 25554-84-1 ]

[ 25554-84-1 ] Synthesis Path-Upstream 1~2

1
[ 1448-87-9 ]
[ 25554-84-1 ]
[ 32601-86-8 ]

Reference： [1] Organic Letters, 2018, vol. 20, # 5, p. 1413 - 1416

2
[ 58-08-2 ]
[ 25554-84-1 ]
[ 832-66-6 ]

Reference： [1] Organic Letters, 2018, vol. 20, # 5, p. 1413 - 1416

Yield	Reaction Conditions	Operation in experiment
75%	In acetone; at 20℃;	A 500 mL round-bottomed flask equipped with a dropping funnel was charged with a magnetic stirrer bar, potassium ethyl xanthogenate (26.77 g5 167 mmol), and acetone (75 mL). A solution of 2-bromoacetic acid (19,31 g, 103 mmol) in acetone (40 mL) was added dropwise at room temperature over a period of 60 min. Stirring was continued overnight at room temperature. Solids were removed by filtration to afford a clear pale yellow solution. The solids on the funnel were washed with acetone (total of 50 mL). The combined washing and filtrate solutions were concentrated under vacuum to furnish a yellow viscous liquid that was dissolved in dichlorometliane (150 mL). This solution was washed twice with brine (100 mL), and the organic phase was dried over MgSO4 and evaporated to dryness to afford 18.75 g (75%) of a white solid. 1H NMR. (400 MHz, CDCl3): delta = 1.43 ( J = 7,32 Hz, 3H), 3.98 (s, 2H) 4.67 (q, J = 7.25 Hz, 2H), 4.53. 13C NMR (100 MHz, CDCl3): delta = 13.68, 37.60, 70.93, 174.30, 212.0.
33%	In acetone; at 20℃; for 16.3333h;	Potassium ethyl xanthogenate (53.06 g, 311 mmol, 1 eqiv.) was stirred acetone (400 mL). A solution of 2-bromoacetic acid (38.35 g, 276 mmol, 1.12 eqiv.) in acetone (100 mL) was added dropwise to the main reaction vessel over 20 minutes and left to stir at ambient temperature for 16 hours. The cmde mixture was filtered under vacuum, washed through with acetone and solvent removed. The residual oil was diluted in dichloromethane and washed with brine (150 mL). The organic layer was dried over Mg504 and solvent removed to give a white solid. Yield:16.28 g, white solid, (33%). ?HNMR (400 MHz, CDC13) = 1.43 (t, 3H), 3.98 (s, 2H), 4.65 (q, 2H), 9.3 (s, br, -OH). ?3C NMR (100 MHz, CDC13) = 13.70, 37.63, 70.93, 173.86, 212.07. Anal. Cald. (C5H80352) = C, 33.32; H, 4.47; 5, 35.58. Found = C, 32.80; H, 4.40; 5, 34.59.

Yield	Reaction Conditions	Operation in experiment
84%	With dicyclohexyl-carbodiimide; 4-(dimethylamino)pyridinium tosylate; In dichloromethane; at 20℃; for 18h;Inert atmosphere;	General procedure for surface group modification to Xanthates (8, 9 and 10) - To a 500mL oven-dried round-bottom flask equipped with a magnetic stirrer (under nitrogen atmosphere), the hydroxyl-terminated dendron (generation 0 through to 3), 2-((Ethoxycarbonothioyl)thio)acetic acid 1, and 4-(Dimethylamino)pyridinium 4-toluenesulfonate (DPTS) were all dissolved in the minimum amount of CH2Cl2. After the reaction flask was flushed with nitrogen, DCC was added. Stirring at room temperature was continued for 18 h under a nitrogen atmosphere. Once the reaction was complete the DCC- urea was filtered off and washed with a small volume of CH2Cl2. The crude product was purified by liquid chromatography on silica gel, eluting with hexane gradually increasing to 40:60 ethyl acetate hexane to give a yellow viscous oil. Synthesis of 8 - 1, 4.65g (25.80 mmol), and 2.72g (8.60 mmol) of 3, 1.01 g (3,44 ramol) of DPTS, and 5.86g (28.38 mmol) of DCC were allowed to react according to the genera esierirkation procedure in 40 mL of dry CH2Cl2 for 18 h. The crude product was purified by liquid chromatography on silica get, eluting with hexane gradually increasing to 40:60 ethyl acetate/hexane to give 6 as a yellow viscous oil 4.6g (84%). 1H NMR (400 MHz, CDCl3): delta = 1.16 (s, 3H), 1.42 (t, J = 7.15, 6H), 2.46 (s, 3H), 3.44 (t, J = 6.3 Hz, 2H), 3.91 (s, 4H), 4.18 (dd, J = 31.72, I 1 .36 Hz, 4H) 4.46 (t, J = 6.03 Hz, 2H), 4.64 (q, 7.12 Hz, 4H), 7.39 (d, J - 8.23, 2H), 7.80 (d, J = 7.70, 2H). 13C NMR (100 MHz, CDC13): delta = 13.74, 17.56, 21.67, 37,70, 54.97, 58.36, 60.39, 66.21, 70.91, 128.12, 130.18, 136.18, 145.28, 167.33, 171.80, 212.57. ES MS: [M + Na]+ = 663.0, [M + K]+ = 679.0.

Yield	Reaction Conditions	Operation in experiment
88%	With dicyclohexyl-carbodiimide; 4-(dimethylamino)pyridinium tosylate; In dichloromethane; at 20℃; for 18h;Inert atmosphere;	General procedure for surface group modification to Xanthates (8, 9 and 10) - To a 500mL oven-dried round-bottom flask equipped with a magnetic stirrer (under nitrogen atmosphere), the hydroxyl-terminated dendron (generation 0 through to 3), 2-((Ethoxycarbonothioyl)thio)acetic acid 1, and 4-(Dimethylamino)pyridinium 4-toluenesulfonate (DPTS) were all dissolved in the minimum amount of CH2Cl2. After the reaction flask was flushed with nitrogen, DCC was added. Stirring at room temperature was continued for 18 h under a nitrogen atmosphere. Once the reaction was complete the DCC- urea was filtered off and washed with a small volume of CH2Cl2. The crude product was purified by liquid chromatography on silica gel, eluting with hexane gradually increasing to 40:60 ethyl acetate hexane to give a yellow viscous oil. Synthesis of 9 - 1, 9.97g (55.32 mtnol), and 5.06g (9.22 mmol) of 5, 2.17g (7.38 mmol) of DPTS, and 1.2.56g (60.85 mmol) of DCC were allowed to react according to the general esterification procedure in 170 mL of dry CH2Cl2 for 18 h. The crude product was purified by liquid chromatography on silica gel, eluting with hexane gradually increasing to 50:50 ethyl acetate/hexane to give 6 as a orange viscous oil 9.65g (88%). 1H NMR (400 MHz, CDCl3): delta = 1.20 (s, 3H), 1.25 (s, 6H), 1.42 (t, J = 7.16, 12H), 2.47 (s, 3H), 3.44 (t, J = 5.97 Hz, 2H), 3.94 (s, 8H), 4.25 (m, I2H) 4.46 (t, J = 5.90 Hz, 2H), 4.64 (q, J= 7.01 Hz, 8H), 7.40 (d, J = 8.51, 2H), 7.82 (d, J = 8.31, 2H).

Yield	Reaction Conditions	Operation in experiment
25%	With 4-methyl-N-methylpyridinium p-toluenesulfonate salt; dicyclohexyl-carbodiimide; In dichloromethane; at 20℃; for 16h;Inert atmosphere;	2-((Ethoxycarbanothioyl)thio) acetic acid, XanCOOH (3.85 g, 21.2 mmol, 1 eqiv), 2- hydroxyethyl 2-bromoisobutyrate (4.5 g, 21.2mmol, 1 eqiv) and 4-(dimethylamino)pyridinium-4- toluene sulphonate (DPTS) (6.86g, 23.32 mmol, 1.1 eqiv) were dissolved in anhydrous dichloromethane (40 mL) under nitrogen. N,N?-Dicyclohexylcarbodiimide (4.81 g, 23.32 mmol, 1.1 eqiv) was dissolved in anhydrous dichloromethane (10 mL) under nitrogen flow and transferred to main reaction vessel via syringe and the reaction was left to stir at ambient temperature for 16 hours. The resulting crude mixture was filtered, diluted in dichlormethane (100 mL) and washed with distilled water (2 x 100 mL) and once with brine (100 mL). The organic layer was dried over MgSO4. After removal of solvents the xanthate initiator was purified by automated liquid chromatography (silica, eluting hexane increasing the polarity to hexane:ethyl acetate 70:30) to give pure product. Yield: 5.08 g, yellow oil, (25%). ?H NIVIR (400 IVIHz, CDC13) = 1.43 (t, 3H), 1.94 (s, 6H), 3.96 (s, 4H), 4.41 (m, 4H), 4.66 (q, 2H). ?3C NIVIR (100 MHz, CDC13) = Calcd. [M+Na](C,,H,7BrO5S2Na) mlz = 395.28. Found: ES MS [M+Na]m/z = 395. Anal. Cald. (C,,H,7BrO5S2) = C, 35.39; H, 4.59; 5, 17.18. Found = C, 36.29; H, 4.79; S, 17.06.

Yield	Reaction Conditions	Operation in experiment
89.9%	With sodium hydroxide; In water; at 20℃; for 72h;	19.7 g (0.10 mol) of dopa was added to the reaction flask.12.0g (0.30mol) of sodium hydroxide,18.0 g (0.20 mol) of <strong>[25554-84-1]S-ethoxythiocarbonylmercaptoacetic acid</strong> (XAA),Dissolved in 150 mL of deionized water,The reaction was stirred for 72 h at room temperature to synthesize 25.8 g of N-ethoxythiocarbonyl substituted dopa (0.09 mol, yield 89.9%).The latter was reacted with PBr3 in ethyl acetate to form a ring to obtain 6.52 g of Dopa-NTA monomer (0.027 mol, yield 30.3%).

Yield	Reaction Conditions	Operation in experiment
58.2%	With sodium hydroxide; In water; at 20℃; for 72h;	36.2 g (0.20 mol) of tyrosine and 32.0 g (0.80 mol) of sodium hydroxide were respectively added to the reaction flask.36.0 g (0.20 mol) of <strong>[25554-84-1]S-ethoxythiocarbonyl thioglycolic acid</strong> (XAA),Dissolved in 150 mL of deionized water,The reaction was stirred for 72 h at room temperature to synthesize 31.3 g of N-ethoxythiocarbonyl-substituted tyrosine (0.12 mol, yield 58.2%).The latter was reacted with PBr3 in ethyl acetate to form a ring to give 9.63 g of Tyr-NTA monomer (0.043 mol, 35.7% yield).

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[ CAS No. 25554-84-1 ] {[proInfo.proName]}

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[ 25554-84-1 ] Synthesis Path-Upstream 1~2

[ 25554-84-1 ] Synthesis Path-Downstream 1~83

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