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CAS No. : | 1155356-49-2 | MDL No. : | MFCD00467415 |
Formula : | C19H18N4O4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | IBOVDNBDQHYNJI-UHFFFAOYSA-N |
M.W : | 366.37 | Pubchem ID : | 4206604 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 | 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 |
---|---|---|
50% | With sodium borate buffer In N,N-dimethyl-formamide at 55℃; for 8h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
200 mg | With dmap In water; N,N-dimethyl-formamide for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | Stage #1: C46H75N6O11P With trifluoroacetic acid In dichloromethane for 1h; Stage #2: 2,5-dioxo-1-pyrrolidinyl 4-[(1E)-2-[4-(dimethylamino)phenyl]diazenyl]-benzoate With TEAB buffer In N,N-dimethyl-formamide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
43% | With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With triethylamine In N,N-dimethyl-formamide at 20℃; for 15h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With triethylamine In N,N-dimethyl-formamide at 20℃; for 15h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With triethylamine In N,N-dimethyl-formamide at 20℃; for 15h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With triethylamine In N,N-dimethyl-formamide at 20℃; for 15h; | |
90% | With triethylamine In N,N-dimethyl-formamide at 20℃; for 15h; | 14 [0058] Dabcyl N-hydroxysuccinimide ester (145 mg, 0.40 mmol) and triethylamine (600 mu L, 4.5 mmol) were added in that order to a dimethylformamide solution (10 mL) of Gly-PNA-OH (100 mg, 0.39 mmol) and stirred at room temperature for 15 hours. After completion of the reaction, the mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (0-4% MeOH/dichloromethane) to give Dabcyl-Gly-PNA-OH (184 mg, 90%) as a reddish brown powder. <1>H NMR (DMSO-d6) delta 8.18 (d, J = 7 Hz, 2 H) , 7.91 (d, J = 7 Hz, 2 H), 7.88 (d, J = 7 Hz, 2 H), 6.77 (d, J = 7 Hz, 2 H), 5.76 (s) and 5.30 (s) (2 H), 4.22 (brs) and 4.05 (brs) (2 H), 3.73 (brs) and 3.49 (brs) (2 H), 3.47 (brs) and 3.29 (brs) (2 H), 1.26 (s, 9 H); FABMS m/z 527 (M+H)<+>]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With triethylamine In N,N-dimethyl-formamide at 20℃; for 15h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 0 - 20℃; for 15.5h; | |
89% | With dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 20℃; | 2,5-Dioxo-1-pyrrolidinyl 4-[(1E)-2-[4-(dimethylamino)phenyl]diazenyl]-benzoate (10) Dabcyl acid (9) (1.48 g, 5.5 mmol) and N-hydroxysuccinimide (0.7 g, 6.0 mmol) were dissolved in anhydrous DMF (80 mL). To the solution, was added a solution of DCC (1.30 g, 6.4 mmol) in DMF (10 mL). The reaction mixture was stirred at room temperature overnight. After filtration, the filtrate was concentrated with an evaporator using an oil pump. The residue was purified with flash column chromatography using silica gel. The eluents were changed from hexane to dichloromethane, and then a mixture of ethyl actate and hexanes (1:4, v/v). The compound 10 was collected as red solid in 89% yield. |
58% | With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0 - 20℃; |
With dicyclohexyl-carbodiimide In N,N-dimethyl-formamide for 16h; | ||
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87 mg | With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: Fmoc-protected cysteine in Wang-resin With piperidine Stage #2: 2,5-dioxo-1-pyrrolidinyl 4-[(1E)-2-[4-(dimethylamino)phenyl]diazenyl]-benzoate In 1-methyl-pyrrolidin-2-one for 1h; Stage #3: With chlorotriisopropylsilane; trifluoroacetic acid Further stages.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: 200 mg / DMAP / dimethylformamide; H2O / 24 h 2.1: carbonyldiimidazole / CHCl3 / 2 h 2.2: 26 percent / DBU / dimethylformamide / 48 h / 4 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: 200 mg / DMAP / dimethylformamide; H2O / 24 h 2.1: carbonyldiimidazole / CHCl3 / 2 h 2.2: 26 percent / DBU / dimethylformamide / 48 h / 4 °C 3.1: 78 percent / methylimidazole; TPSNT / CH2Cl2 / 24 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: 200 mg / DMAP / dimethylformamide; H2O / 24 h 2.1: carbonyldiimidazole / CHCl3 / 2 h 2.2: 26 percent / DBU / dimethylformamide / 48 h / 4 °C 3.1: 78 percent / methylimidazole; TPSNT / CH2Cl2 / 24 h / 20 °C 4.1: TFA / CH2Cl2 / 1 h 4.2: 76 percent / TEAB buffer / dimethylformamide / pH 8.4 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: 200 mg / DMAP / dimethylformamide; H2O / 24 h 2.1: carbonyldiimidazole / CHCl3 / 2 h 2.2: 26 percent / DBU / dimethylformamide / 48 h / 4 °C 3.1: 78 percent / methylimidazole; TPSNT / CH2Cl2 / 24 h / 20 °C 4.1: TFA / CH2Cl2 / 1 h 4.2: 76 percent / TEAB buffer / dimethylformamide / pH 8.4 5.1: 50 percent / Streptomyces sp. PLD(P); NaOAc; CaCl2 / CHCl3 / 45 °C / pH 5.4 6.1: TFA / CHCl3 | ||
Multi-step reaction with 3 steps 1.1: TFA / CH2Cl2 / 1 h 1.2: 76 percent / TEAB buffer / dimethylformamide / pH 8.4 2.1: 50 percent / Streptomyces sp. PLD(P); NaOAc; CaCl2 / CHCl3 / 45 °C / pH 5.4 3.1: TFA / CHCl3 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: 200 mg / DMAP / dimethylformamide; H2O / 24 h 2.1: carbonyldiimidazole / CHCl3 / 2 h 2.2: 26 percent / DBU / dimethylformamide / 48 h / 4 °C 3.1: 78 percent / methylimidazole; TPSNT / CH2Cl2 / 24 h / 20 °C 4.1: TFA / CH2Cl2 / 1 h 4.2: 76 percent / TEAB buffer / dimethylformamide / pH 8.4 5.1: 50 percent / Streptomyces sp. PLD(P); NaOAc; CaCl2 / CHCl3 / 45 °C / pH 5.4 | ||
Multi-step reaction with 2 steps 1.1: TFA / CH2Cl2 / 1 h 1.2: 76 percent / TEAB buffer / dimethylformamide / pH 8.4 2.1: 50 percent / Streptomyces sp. PLD(P); NaOAc; CaCl2 / CHCl3 / 45 °C / pH 5.4 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With pyridine; dmap In toluene at 20℃; for 24h; | |
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With triethylamine In N,N-dimethyl-formamide at 20℃; for 12h; | Ethyl N-[4-[(1E)-2-[4-(dimethylamino)phenyl] diazenyl]benzoyl]-glycinate (6) To a solution of ethyl glycinate hydrochloride (0.416 g, 2.98 mmol) in DMF (50 mL), were added triethylamine (0.414 mL, 3 mmol) and compound 10 (0.91 g, 2.48 mmol). The resulted mixture was stirred at rt for 12 h, and then concentrated with an evaporator equipped with an oil pump. The residue was purified with flash column chromatography (SiO2; 0-7.5% EtOAc/CH2Cl2) to afford 6 as an orange solid (0.78 g, 88%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: triethylamine / N,N-dimethyl-formamide / 12 h / 20 °C 2.1: lithium hydroxide / tetrahydrofuran; methanol / 3 h 2.2: pH 2 - 3 3.1: caesium carbonate / tetrahydrofuran; methanol; water / 0.5 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: triethylamine / N,N-dimethyl-formamide / 12 h / 20 °C 2.1: lithium hydroxide / tetrahydrofuran; methanol / 3 h 2.2: pH 2 - 3 3.1: caesium carbonate / tetrahydrofuran; methanol; water / 0.5 h 4.1: copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine; triphenylphosphine / N,N-dimethyl-formamide / 3 h / 70 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: triethylamine / N,N-dimethyl-formamide / 12 h / 20 °C 2.1: lithium hydroxide / tetrahydrofuran; methanol / 3 h 2.2: pH 2 - 3 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47.7 mg | With N-ethyl-N,N-diisopropylamine at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
10.6 mg | With N-ethyl-N,N-diisopropylamine at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine In N,N-dimethyl-formamide at 0 - 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
242 mg | With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 12h; | 2 (E)-2,5-Dioxopyrrolidin-1-yl 4-((4-(dimethylamino)phenyl)diazenyl)-benzoate (200 mg) was mixed with dimethyl formamide (5 mL), tert-butyl 1-(2-aminoethylamino)-1-oxo-3-(tritylthio)propan-2-ylcarbamate (333 mg), and diisopropylethylamine (285 μL). After 12 hours, the reaction was partitioned between ethyl acetate and aqueous citric acid. The organic layer was washed with bicarbonate and, then, brine. After evaproration, the residue was eluted through silica with heptane: ethyl acetate (1:1). Yield: 242 mg. |
242 mg | With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 12h; | 2 (E)-2,5-Dioxopyrrolidin-1-yl 4-((4-(dimethylamino)phenyl)diazenyl)-benzoate (200 mg) was mixed with dimethyl formamide (5 mL), tert-butyl 1-(2-aminoethylamino)-1-oxo-3-(tritylthio)propan-2-ylcarbamate (333 mg), and diisopropylethylamine (285 μL). After 12 hours, the reaction was partitioned between ethyl acetate and aqueous citric acid. The organic layer was washed with bicarbonate and, then, brine. After evaproration, the residue was eluted through silica with heptane: ethyl acetate (1:1). Yield: 242 mg |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 12 h 2: chlorotriisopropylsilane; trifluoroacetic acid / water / 12 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: water; N,N-dimethyl-formamide / 24 h / 50 °C / pH 9 2: Novozym 435 / acetonitrile / 40 °C / Molecular sieve |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: water; N,N-dimethyl-formamide / 24 h / 50 °C / pH 9 2.1: 1,1'-carbonyldiimidazole / dimethyl sulfoxide / 0.5 h 2.2: 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In water; N,N-dimethyl-formamide at 50℃; for 24h; | sn-Glycero-3-(N-dabcyl-phosphoethanolamine) (3) Dabcyl NHS-ester (100 mg, 0.273 mmol) was dissolved in DMF(5 mL). The crude freeze-dried GPE (2) was dissolved in 0.1 Mcarbonate buffer pH 9.0 (5 mL) and added to the dabcyl NHS-estersolution. The reaction was stirred at 50 C and followed with TLC inEtOAc-heptane (1:1). After 24 h, the solvent was evaporated undervacuum and the crude product purified byflash chromatographywith dry loading. Hence, it was redissolved in DCM:MeOH:H2O(15:6:1) and two spoons of Kieselgel 60 (0.063-0.200 mm) wereadded. This was followed by a second evaporation under vacuum.The product was added on top of a 50 g Biotage SNAP cartridge, andpurified using a gradient of MeOH in DCM:NEt3 (8:1) from 0 to 40%.Yield 118 mg orange GPE-dabcyl (3) as the NEt3 salt, 66% over twosteps from PE (1).1H NMR (CD3OD): 8.01 (d, J = 8.8 Hz, 2H, dabcyl), 7.88 (d,J = 5.9 Hz, 2H, dabcyl), 7.86 (d, J = 5.4 Hz, 2H, dabcyl), 6.86 (d,J = 9.2 Hz, 2H, dabcyl), 4.13-4.07 (m, 2H,CH2CH2NH-), 3.99-3.87(m, 2H, H-3), 3.81-3.76 (m,1H, H-2), 3.67 (t, J = 5.3 Hz, 2H,CH2NH-), 3.59 (dd, J = 5.1, 13.8 Hz, 2H, H-1), 3.13 (s, 6H,NMe2). 13C NMR (CD3OD): 168.2 (-NH-CO-), 155.0 (dabcyl quaternaryC), 153.3 (dabcyl quaternary C), 143.5 (dabcyl quaternary C), 134.3(dabcyl quaternary C),128.0 (dabcyl),125.0 (dabcyl),121.5 (dabcyl),111.2 (dabcyl), 71.1 (C-2), 66.2 (C-3), 63.4 (-CH2CH2NH-), 62.4 (C-1),40.8 (-CH2NH-), 39.1 (-NMe2).ESI-MS (calculated for C20H27N4O7P, 466.16): m/z 467.00 [M+H]+, 932.87 [2M+H]+, 955.13 [2M+Na]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C 2: copper(II) sulfate; ascorbic acid / N,N-dimethyl-formamide / 2 h / 40 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C 2: copper(II) sulfate; ascorbic acid / N,N-dimethyl-formamide / 2 h / 40 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C 2: copper(II) sulfate; ascorbic acid / N,N-dimethyl-formamide / 2 h / 40 °C 3: human acyl protein thioesterases 1 / aq. phosphate buffer / 37 °C / pH 7.4 / Enzymatic reaction |