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CAS No. : | 4294-16-0 | MDL No. : | MFCD00005740 |
Formula : | C17H19N5O4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | MRPKNNSABYPGBF-LSCFUAHRSA-N |
M.W : | 357.36 | Pubchem ID : | 92208 |
Synonyms : |
Benzyladenosine;DNPH1i;BAPR
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-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 |
---|---|---|
22% | With bromine; sodium acetate; acetic acid In water at 45℃; for 2.5 h; | 6-Benzylamino-9-(β-D-ribofuranosyl)purine (469.4 mg; 1.313 mmol) was suspended in 15 ml 1 M AcONa and 15 ml 1 M AcOH. Bromine water (12.7 ml) was added to suspension and mixture was heated for 2.5 h at 45° C. Excess bromine was eliminated by addition of solid NaHSO3 and then the mixture was neutralized by 10percent NaOH and evaporated. Residue was shaken out with water and chloroform. Organic layer was separated, dried in MgSO4 and after filtration of desiccant evaporated to dryness. The residue was purified by column chromatography in CHCl3-MeOH-NH4OH (95:5:0.5). Yield 126.5 mg 6-benzylamino-8-bromo-9-(β-D-ribofuranosyl)purine (22percent), 42.2 mg starting material (9percent), 205 mg 8-bromoadenosine (45percent) and mixture of benzaldehyde and bromobenzaldehyde. Crystallization from CHCl3-hexan; mp: 98-100° C. MS ESI+: 436.2 [M+H+]. For C17H13BrN5O4 calculated 435.0542, found 436.0680 [M+H+]. 1H NMR (400 MHz; CDCl3) δ 3.75 (dd, J=2.7 Hz, 12.7 Hz, H5′), 3.90 (dd, J=2.4 Hz, 12.7 Hz, H5′), 4.20 (d, J=1.8 Hz, H4′), 4.39 (dd, J=1.8 Hz, 5.3 Hz, H3′), 4.81 (bs, —CH2—), 5.08 (dd, J=5.3 Hz, 7.2 Hz, H2′), 6.07 (d, J=7.2 Hz, H1′), 7.24 (m, H4-Ph), 7.31 (m, H3-Ph), 7.38 (m, H2-Ph), 8.19 (s, H2). MS ESI+ (8-bromoadenosine): 346.3 [M+H+]. GC: Rt (benzaldehyde)=321 s. MS EI (benzyldehyde): 105 (100percent), 77 (25percent). Rt (bromobenzyldehyde)=722 s. MS EI: 185 (100percent), 155 (50percent), 77 (45percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
20% | With N-chloro-succinimide In N,N-dimethyl-formamide at 45℃; for 18 h; | 6-Benzylamino-9-(β-D-ribofuranosyl)purine (115 mg, 0.322 mmol) and 51.6 mg (0.386 mmol) N-chlorosuccinimide was dissolved in 3 ml DMF and the solution was heated at 45° C. for 18 h. The mixture was evaporated and residue was purified by column chromatography in CHCl3-MeOH-NH4OH (95:5:0.5). Yield 25.2 mg 6-benzylamino-8-chloro-9-(β-D-ribofuranosyl)purine (20percent) a 62.1 mg starting compound (54percent); mp=90-92° C. MS ESI+: 392.2 [M+H+]. For C17H18ClN5O4 calculated 391.1047, found 392.1119 [M+H+]. 1H NMR (300 MHz; CDCl3) δ 3.61 (dd, J=4.1 Hz, 8.2 Hz, H5'), 3.89 (d, J=12.7 Hz, H5'), 4.27 (s, H4'), 4.45 (d, J=5.7 Hz, H3'), 4.74 (bs, -CH2-), 4.79 (bs, -CH2-), 5.00 (dd, J=5.7 Hz, 6.3 Hz, H2'), 6.01 (d, J=7.3 Hz, H1'), 6.38 (bs, H-N), 7.28 (m, H-Ph), 8.21 (s, H2). 8-Chloroadenosine was isolated as an analytical sample for MS ESI by wash out from TLC. MS ESI+: 302.3 [M+H+]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ammonia In methanol Yield given; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With triethylamine; In neat (no solvent); at 210℃; under 12929.0 Torr; for 0.0166667h;Irradiation; | Synthesis of (2R, 3R, 4S, 5R)-2-(6-(benzylamino)-9H-purin-9-yl)-5-(hydroxymethyl) tetrahydrofuran-3,4-diol, 2. In a 7 mL MW vessel, 6-chloropurinoriboside 3 (20 mg, 0.07 mmol), benzylamine 4 (7.5 mg,0.07 mmol, 7.7 muL) and triethylamine (7.08 mg, 0.07 mmol, 9.8 muL)were mixed. The solid mixture was stirred in CEM Explorer. MWMethod: T = 210 C, Power: 300 W, Hold Time: 1 min, P = 250 PSI,Power Max activated. After cooling, the solvent was removed in vacuoand the crude was dissolved in methanol and then purified on PTLC(DCM/MeOH 9:1) to afford compound 2 as white solid (24 mg, 94%).1H NMR (600 MHz, MeOD) delta 8.30 (s, 1H), 8.28 (s, 1H), 7.43 (d,J=7.5 Hz, 2H), 7.36 (t, J=7.6 Hz, 2H), 7.29 (t, J=7.3 Hz, 1H), 6.01(d, J = 6.4 Hz, 1H), 4.82-4.77 (m, 1H), 4.37 (dd, J = 4.9, 2.5 Hz, 1H),4.22 (d, J = 2.4 Hz, 1H), 3.93 (dd, J = 12.5, 2.3 Hz, 1H), 3.79 (dd,J = 12.5, 2.5 Hz, 1H) ppm. HRMS (ESI-Q-TOF) m/z [M + H] + Calcd.for C17H20N5O4: 358.1510; Found 358.1515. Rt: 8.92 min. |
80% | With triethylamine; In ethanol; at 60℃; for 18h; | A mixture of 5a (100mg, 0.35 mmol), benzylamine (0.04m1, 0.35mmol), Et3N(0.05m1, 0.35mmol) in ethanol (5mL) was stirred at 60 C for 18 h. After cooled to roomtemperature, the reaction mixture was concentrated in vacuo and the residue was purified by column chromatography to give the title product Sb as white solids (100.5mg, 80%): MS (ESI): m/z =358 [M+H] 1H NMR (500 MHz, DMSO-d6) 8.49 (s, 1H), 8.38 (s, 1H), 8.20 (s, 1H), 7.33-7.27 (m, 4H), 7.22-7.19 (m, 1H), 5.88 (d, J= 6.2 Hz, 1H), 5.46 (d, J= 6.1 Hz,1H), 5.41-5.38 (m, 1H), 5.20 (d, J= 6.2 Hz, 1H), 4.70 (s, 2H), 4.63-4.60 (m, 1H), 4.14 (d, J =3.0 Hz, 1H), 3.96 (d, J= 3.0 Hz, 1H), 3.67 (d, J 12.1 Hz, 1H), 3.54 (ddd, J 11.7, 7.2, 3.5 Hz, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 59% 2: 39% | In N,N-dimethyl-formamide at 0℃; for 1h; | |
1: 25% 2: 55% | With bis(tri-n-butyltin)oxide In N,N-dimethyl-formamide; acetonitrile at 0℃; for 1h; | |
1: 12 % Chromat. 2: 87 % Chromat. | In N,N-dimethyl-formamide; toluene |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | With bis(tri-n-butyltin)oxide In N,N-dimethyl-formamide; toluene at 0℃; for 46h; Yields of byproduct given; | |
1: 18% 2: 6 % Chromat. 3: 15% 4: 60 % Chromat. | In N,N-dimethyl-formamide; toluene for 2h; Ambient temperature; variation of purine and pyrimidine ribonucleoside, catalyst, solvent and reaction condition; | |
1: 18% 2: 6 % Chromat. 3: 15% 4: 60 % Chromat. | In N,N-dimethyl-formamide; toluene for 2h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With bis(tri-n-butyltin)oxide In toluene 1.) reflux, 4 h; 2.) rt., 1 h; | |
70% | 1.) PhMe, reflux; 2.) RT; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 22% 2: 23% 3: 39% 4: 8% | With bis(tri-n-butyltin)oxide In toluene 1.) reflux, 4 h; 2.) rt., 3 h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With Zn naphthenate In N,N-dimethyl-formamide at -17℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | With bis(tri-n-butyltin)oxide In toluene 1.) reflux, 4 h; 2.) rt., 19 h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With ammonium peroxydisulfate; phosphate buffer at 80℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; | |
95% | With ammonium sulfate; 1,1,1,3,3,3-hexamethyl-disilazane Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; sodium cyanoborohydride In methanol; water at 37℃; for 28h; pH 4.4; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With pyridine for 20h; | |
85% | With pyridine for 20h; Ambient temperature; | |
85% | With pyridine |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With pyridine; thionyl chloride In acetonitrile at 5 - 20℃; | |
64% | With pyridine; thionyl chloride In acetonitrile at 0 - 25℃; | |
With N,N,N,N,N,N-hexamethylphosphoric triamide; thionyl chloride |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | at 75℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With pyridine In tetrahydrofuran at 0 - 20℃; for 8.16667h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: N6-Benzyladenosine With trimethyl phosphite; Proton Sponge; trichlorophosphate at 4℃; Stage #2: With pyridine; Phosphoric acid tri-n-butylammonium salt at 0℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With 3-chloro-benzenecarboperoxoic acid In methanol at 37℃; for 42h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 80 percent / pyridine / tetrahydrofuran / 8.17 h / 0 - 20 °C 2: 56 percent / methanesulfonic acid / dimethylformamide / 24 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 80 percent / pyridine / tetrahydrofuran / 8.17 h / 0 - 20 °C 2: 56 percent / methanesulfonic acid / dimethylformamide / 24 h / 0 - 20 °C 3: 90 percent / triphenylphosphine; diethyl azodicarboxylate / tetrahydrofuran / 2.5 h / 20 °C 4: K2CO3; thiophenol / dimethylformamide / 12 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 80 percent / pyridine / tetrahydrofuran / 8.17 h / 0 - 20 °C 2: 56 percent / methanesulfonic acid / dimethylformamide / 24 h / 0 - 20 °C 3: 90 percent / triphenylphosphine; diethyl azodicarboxylate / tetrahydrofuran / 2.5 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: SOCl2; HMPA 2: KI / H2O / Heating | ||
Multi-step reaction with 2 steps 1.1: pyridine; thionyl chloride / acetonitrile / 0 - 25 °C 2.1: sodium hydroxide / water / 1.5 h / 100 °C / Inert atmosphere 2.2: 16 h / 100 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: SOCl2; HMPA 2: KI / H2O / Heating 3: AgClO4; HCO2H; AcOH |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 141 mg / NH3 / methanol / 2 h / 0 °C 2: 100 percent / 24 h / 75 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 97 percent / SOCl2, pyridine / acetonitrile / 5 - 20 °C 2: 74 percent / aq. NaOH / dimethylformamide / 2 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 97 percent / SOCl2, pyridine / acetonitrile / 5 - 20 °C 2: 61 percent / aq. NaOH / dimethylformamide / 2 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 97 percent / SOCl2, pyridine / acetonitrile / 5 - 20 °C 2: 80 percent / aq. NaOH / dimethylformamide / 2 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 97 percent / SOCl2, pyridine / acetonitrile / 5 - 20 °C 2: 87 percent / aq. NaOH / dimethylformamide / 2 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 85 percent / pyridine / 20 h / Ambient temperature 2: 38 percent / Et3N, DMAP / acetonitrile / 18 h / Ambient temperature 3: TsOH / methanol; CH2Cl2 / 0.17 h | ||
Multi-step reaction with 3 steps 1: 85 percent / pyridine / 20 h 2: 38 percent / Et3N, 4-dimethylaminopyridine / acetonitrile 3: 95 percent / TsOH / CH2Cl2; methanol / 0.17 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 85 percent / pyridine / 20 h / Ambient temperature 2: 13 percent / Et3N, DMAP / acetonitrile / 18 h / Ambient temperature | ||
Multi-step reaction with 2 steps 1: 85 percent / pyridine / 20 h 2: 13 percent / Et3N, 4-dimethylaminopyridine / acetonitrile |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 85 percent / pyridine / 20 h / Ambient temperature 2: 46 percent / Et3N, DMAP / acetonitrile / 18 h / Ambient temperature | ||
Multi-step reaction with 2 steps 1: 85 percent / pyridine / 20 h 2: 46 percent / Et3N, 4-dimethylaminopyridine / acetonitrile |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 85 percent / pyridine / 20 h / Ambient temperature 2: 38 percent / Et3N, DMAP / acetonitrile / 18 h / Ambient temperature | ||
Multi-step reaction with 2 steps 1: 85 percent / pyridine / 20 h 2: 38 percent / Et3N, 4-dimethylaminopyridine / acetonitrile |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: 85 percent / pyridine / 20 h / Ambient temperature 2: 46 percent / Et3N, DMAP / acetonitrile / 18 h / Ambient temperature 3: pyridine / 3 h 4: 18 h / Ambient temperature 5: 4-nitrobenzaldoxim / dioxane; H2O / 20 h / 4 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 85 percent / pyridine / 20 h / Ambient temperature 2: 46 percent / Et3N, DMAP / acetonitrile / 18 h / Ambient temperature 3: pyridine / 3 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 85 percent / pyridine / 20 h / Ambient temperature 2: 46 percent / Et3N, DMAP / acetonitrile / 18 h / Ambient temperature 3: pyridine / 3 h 4: 18 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 85 percent / pyridine / 20 h 2: 46 percent / Et3N, 4-dimethylaminopyridine / acetonitrile 3: 1.) pyridine / 1.) 0 deg C, 3 h, 2.) 18 h 4: 4-nitrobenzaldoxime, Et3N / dioxane; H2O / 4 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 85 percent / pyridine / 20 h 2: 46 percent / Et3N, 4-dimethylaminopyridine / acetonitrile 3: 1.) pyridine / 1.) 0 deg C, 3 h, 2.) 18 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: I2 / 0.5 h / 190 - 195 °C 2: NH3 / methanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With toluene-4-sulfonic acid at 20℃; for 0.75h; | |
With thionyl chloride; trimethyl orthoformate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With toluene-4-sulfonic acid In acetone at 25℃; for 24h; | |
67% | With toluene-4-sulfonic acid In acetone at 20℃; for 16h; | 5B Step 5B A mixture of Sb (2.8g, 7.8mmol), 2,2-dimethoxypropane (lOmL, 81.8mmol), and p15 toluenesulfonic acid monohydrate (1.86g, 9.8mmol) in acetone (78mL) was stirred at roomtemperature for 16 h. Then, sodium bicarbonate (2.6g, 3 1.4mmol) and water (SOmL) were added, and the reaction mixture was stirred for 2h. The reaction mixture was extracted with ethyl acetate (3xlOOmL). The combined organic layers were dried over anhy. sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by column chromatography togive Sc as white solids (2. lg, 67%): MS (ESI): m/z =398 [M+H]+ |
280 mg | With toluene-4-sulfonic acid In acetone at 20℃; for 16h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With trichlorophosphate In trimethyl phosphite |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 20 h / 20 °C 2: methanol; ammonia / 48 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With methanol; ammonia at 20℃; for 48h; | |
With ammonia In methanol at 20℃; for 48h; | ||
With propylamine In methanol at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 20 h / 20 °C 2: methanol; ammonia / 48 h / 20 °C | ||
Multi-step reaction with 2 steps 1: barium carbonate; potassium iodide / N,N-dimethyl-formamide / 24 h / 65 °C 2: ammonium hydroxide / 168 h / 20 °C | ||
Multi-step reaction with 3 steps 1.1: barium carbonate; potassium iodide / N,N-dimethyl-formamide / 24 h / 65 °C 2.1: pyridine / 24 h 3.1: ammonia / methanol / 120 h / 20 °C 3.2: 168 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: pyridine / 20 - 60 °C 2: potassium carbonate / N,N-dimethyl-formamide / 20 h / 20 °C 3: methanol; ammonia / 48 h / 20 °C | ||
Multi-step reaction with 3 steps 1.1: pyridine / 20 - 60 °C 1.2: 20 °C 2.1: potassium carbonate / N,N-dimethyl-formamide / 20 h / 20 °C 3.1: methanol; ammonia / 48 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: thionyl chloride; trimethyl orthoformate 2: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 2.5 h 3: hydrazine hydrate / ethanol / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: thionyl chloride; trimethyl orthoformate 2: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 2.5 h | ||
Multi-step reaction with 2 steps 1: toluene-4-sulfonic acid / acetone / 16 h / 20 °C 2: triphenylphosphine / tetrahydrofuran / 0.17 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: thionyl chloride; trimethyl orthoformate 2: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 2.5 h 3: hydrazine hydrate / ethanol / Reflux 4: triethylamine / tetrahydrofuran |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: pyridine / methanol / 4 h 2.1: dmap; trichlorophosphate / 0.12 h / 20 °C / Inert atmosphere 2.2: 0.22 h / Reflux 3.1: ammonia / methanol / 19 h / 0 - 20 °C 4.1: triethylamine / ethanol / 18 h / 60 °C | ||
Multi-step reaction with 3 steps 1: triethylamine / acetonitrile / 6 h / 0 °C / Reflux 2: ammonia / methanol 3: triethylamine / ethanol / 24 h / 78 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: ammonia / methanol / 19 h / 0 - 20 °C 2: triethylamine / ethanol / 18 h / 60 °C | ||
Multi-step reaction with 2 steps 1: ammonia / methanol 2: triethylamine / ethanol / 24 h / 78 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: hydroxylamine hydrochloride; sodium acetate / ethanol / 6 h / 20 °C 2: hydrogenchloride; hydrogen / palladium 10% on activated carbon / ethanol; water / 760.05 Torr 3: N-ethyl-N,N-diisopropylamine / propan-1-ol / 8 h / 70 °C | ||
Multi-step reaction with 3 steps 1: hydroxylamine hydrochloride; sodium acetate / ethanol / 6 h / 20 °C 2: hydrogenchloride; hydrogen; palladium 10% on activated carbon / ethanol / 760.05 Torr 3: N-ethyl-N,N-diisopropylamine / propan-1-ol / 8 h / 70 °C | ||
Multi-step reaction with 3 steps 1: hydroxylamine hydrochloride; sodium acetate / ethanol / 6 h / 20 °C 2: hydrogenchloride; palladium 10% on activated carbon; hydrogen / ethanol; water 3: N-ethyl-N,N-diisopropylamine / propan-1-ol / 8 h / 70 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-ethyl-N,N-diisopropylamine In propan-1-ol at 70℃; for 8h; | 1 First step, benzaldehyde (1.08 g), hydroxyamine hydrochloride (1.29 g), and NaOAc (1.67 g) were dissolved in EtOH (40 ml). The reaction mixture was stirred at room temperature for 6 h. EtOH was removed under reduced pressure. H2O (20 ml) was added to the residue, and extracted with EtOAc (3 × 20 ml). The EtOAc of the combined organic layer was removed by a rotary evaporation under reduced pressure to yield benzaldehyde oxime (1.13 g) as a pale yellowish solid. Second step, a solution of benzaldehyde oxime (1.13 g) and concentrated HCl (1 ml) in EtOH (40 ml) was subjected to hydrogenation at atmospheric pressure in the presence of 10% Pd/C (85 mg). The reaction mixture was filtered and the filtrate was concentrated to yield benzylamine hydrochloride (1.29 g) as a white solid. Third step, a mixture of benzylamine (355 mg, the hydrochloride), 6-chloropurine riboside (143 mg), and N,N-diisopropylethylamine (2 ml) in PrOH (40 ml) was heated to 70°C and reacted for 8h. After evaporation of the reaction mixture, the residue was separated by column chromatography oversilica gel eluting with CHCl3-CH3OH (30 : 1) to yield N6-(benzyl)-adenosine(151 mg) as a colorless solid: positive ESIMS at m/z 358 [M + H]+; negative ESIMS at 356 [M - H]- and 392 [M + Cl]-; 1H NMR (300 MHz, CD3OD): the adenosine moiety δ 8.20 (1H, s, H-2), 8.18 (1H, brs, H-8), 5.90 (1H, d, J = 6.6 Hz, H-1, H-1'), 4.69 (1H, dd, J= 6.6, 5.4 Hz, H-2'), 4.26 (1H, dd, J= 5.4 and 2.4 Hz, H-3'), 4.11 (1H, q, J = 2.4 Hz, H-4'), 3.83 (1H, dd, J = 12.6 and 2.4 Hz, H-5'a), 3.68 (1H, dd, J = 12.6 and 2.4 Hz, H-5'b); the benzyl moiety δ 7.14-7.34 (5H, m, H-2" ∼ H-6"), 4.77 (2H, brs, H-7"); 13C NMR (75 MHz, DMSO-d6): the adenosine moiety δ 154.6 (C-6), 152.4 (C-2), 148.5 (C-4), 140.0 (C-8), 119.8 (C-5), 88.0 (C-1'), 85.9 (C-4'), 73.5 (C-2'), 70.7 (C-3'), 61.7 (C-5'); the benzyl moiety δ 128.2 (C-3", C-5"), 127.1 (C-2", C-6"), 126.6 (C-4"), 42.9 (C-7"). | |
151 mg | With N-ethyl-N,N-diisopropylamine In propan-1-ol at 70℃; for 8h; | 1 Preparation of N6-(benzyl)-adenosine Third step, a mixture of benzylamine (355 mg, the hydrochloride), 6-chloropurine riboside (143 mg), and N,N-diisopropylethylamine (2 ml) in PrOH (40 ml) was heated to 70° C. and reacted for 8 h. After evaporation of the reaction mixture, the residue was separated by column chromatography oversilica gel eluting with CHCl3-CH3OH (30:1) to yield N6-(benzyl)-adenosine (151 mg) as a colorless solid: positive ESIMS at m/z 358 [M+H]+: negative ESIMS at 356 [M-H]- and 392 [M+Cl]-; 1H NMR (300 MHz, CD3OD): the adenosine moiety δ 8.20 (1H, s, H-2), 8.18 (1H, brs, H-8), 5.90 (1H, d, J=6.6 Hz, H-1, H-1'), 4.69 (1H, dd, J=6.6, 5.4 Hz, H-2'), 4.26 (1H, dd, J=5.4 and 2.4 Hz, H-3'), 4.11 (1H, q, J=2.4 Hz, H-4'), 3.83 (1H, dd, J=12.6 and 2.4 Hz, H-5'a), 3.68 (1H, dd, J=12.6 and 2.4 Hz, H-5'b); the benzyl moiety δ 7.14-7.34 (5H, m, H-2"˜H-6"), 4.77 (2H, brs, H-7"); 13C NMR (75 MHz, DMSO-d6): the adenosine moiety δ 154.6 (C-6), 152.4 (C-2), 148.5 (C-4), 140.0 (C-8), 119.8 (C-5), 88.0 (C-1'), 85.9 (C-4'), 73.5 (C-2'), 70.7 (C-3'), 61.7 (C-5'); the benzyl moiety δ 128.2 (C-3", C-5"), 127.1 (C-2", C-6"), 126.6 (C-4"), 42.9 (C-7"). |
151 mg | With N-ethyl-N,N-diisopropylamine In propan-1-ol at 70℃; for 8h; | 1.3 Third step 335 mg of benzylamine hydrochloride was taken, dissolved in propanol (40 mL), and 6-chloropurine nucleoside (143 mg) and N, N-diisopropylethylamine base (2 mL) were added and heated to 70 ° C, reacted for 8 hours, recovered the solvent in the reaction solution, Separation by silica gel column chromatography, washed off with chloroform-methanol (30: 1), to obtain 151 mg of colorless solid N6-(benzyl)-adenosine, |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: hydrogenchloride; hydrogen / palladium 10% on activated carbon / ethanol; water / 760.05 Torr 2: N-ethyl-N,N-diisopropylamine / propan-1-ol / 8 h / 70 °C | ||
Multi-step reaction with 2 steps 1: hydrogenchloride; hydrogen; palladium 10% on activated carbon / ethanol / 760.05 Torr 2: N-ethyl-N,N-diisopropylamine / propan-1-ol / 8 h / 70 °C | ||
Multi-step reaction with 2 steps 1: hydrogenchloride; palladium 10% on activated carbon; hydrogen / ethanol; water 2: N-ethyl-N,N-diisopropylamine / propan-1-ol / 8 h / 70 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sodium acetate; acetic acid; bromine / water / 2.5 h / 45 °C 2: sodium / 19 h / 20 °C | ||
Multi-step reaction with 3 steps 1: sodium acetate; acetic acid; bromine / water / 2.5 h / 45 °C 2: N,N-dimethyl-formamide / 24 h / 50 °C / Molecular sieve 3: sodium / 19 h / 20 °C | ||
Multi-step reaction with 4 steps 1: sodium acetate; acetic acid; bromine / water / 2.5 h / 45 °C 2: N,N-dimethyl-formamide / 6 h / 20 °C 3: acetic acid; potassium permanganate / 0.75 h / -5 °C 4: sodium hydroxide / 1 h / 20 °C |
Multi-step reaction with 5 steps 1: sodium acetate; acetic acid; bromine / water / 2.5 h / 45 °C 2: N,N-dimethyl-formamide / 24 h / 50 °C / Molecular sieve 3: N,N-dimethyl-formamide / 6 h / 20 °C 4: acetic acid; potassium permanganate / 0.75 h / -5 °C 5: sodium hydroxide / 1 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
20% | With N-chloro-succinimide In N,N-dimethyl-formamide at 45℃; for 18h; | 3 6-Benzylamino-8-chloro-9-(β-D-ribofuranosyl)purine. 6-Benzylamino-9-(β-D-ribofuranosyl)purine (115 mg, 0.322 mmol) and 51.6 mg (0.386 mmol) N-chlorosuccinimide was dissolved in 3 ml DMF and the solution was heated at 45° C. for 18 h. The mixture was evaporated and residue was purified by column chromatography in CHCl3-MeOH-NH4OH (95:5:0.5). Yield 25.2 mg 6-benzylamino-8-chloro-9-(β-D-ribofuranosyl)purine (20%) a 62.1 mg starting compound (54%); mp=90-92° C. MS ESI+: 392.2 [M+H+]. For C17H18ClN5O4 calculated 391.1047, found 392.1119 [M+H+]. 1H NMR (300 MHz; CDCl3) δ 3.61 (dd, J=4.1 Hz, 8.2 Hz, H5'), 3.89 (d, J=12.7 Hz, H5'), 4.27 (s, H4'), 4.45 (d, J=5.7 Hz, H3'), 4.74 (bs, -CH2-), 4.79 (bs, -CH2-), 5.00 (dd, J=5.7 Hz, 6.3 Hz, H2'), 6.01 (d, J=7.3 Hz, H1'), 6.38 (bs, H-N), 7.28 (m, H-Ph), 8.21 (s, H2). 8-Chloroadenosine was isolated as an analytical sample for MS ESI by wash out from TLC. MS ESI+: 302.3 [M+H+]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sodium acetate; acetic acid; bromine / water / 2.5 h / 45 °C 2: methanol; water / 18 h / 20 °C | ||
Multi-step reaction with 3 steps 1: sodium acetate; acetic acid; bromine / water / 2.5 h / 45 °C 2: N,N-dimethyl-formamide / 24 h / 50 °C / Molecular sieve 3: methanol; water / 18 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: sodium acetate; acetic acid; bromine / water / 2.5 h / 45 °C 2: N,N-dimethyl-formamide / 6 h / 20 °C 3: acetic acid; potassium permanganate / 0.75 h / -5 °C | ||
Multi-step reaction with 4 steps 1: sodium acetate; acetic acid; bromine / water / 2.5 h / 45 °C 2: N,N-dimethyl-formamide / 24 h / 50 °C / Molecular sieve 3: N,N-dimethyl-formamide / 6 h / 20 °C 4: acetic acid; potassium permanganate / 0.75 h / -5 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sodium acetate; acetic acid; bromine / water / 2.5 h / 45 °C 2: sodium hydrogen sulfide / N,N-dimethyl-formamide / 6 h / 20 °C | ||
Multi-step reaction with 3 steps 1: sodium acetate; acetic acid; bromine / water / 2.5 h / 45 °C 2: N,N-dimethyl-formamide / 24 h / 50 °C / Molecular sieve 3: sodium hydrogen sulfide / N,N-dimethyl-formamide / 6 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sodium acetate; acetic acid; bromine / water / 2.5 h / 45 °C 2: N,N-dimethyl-formamide / 6 h / 20 °C | ||
Multi-step reaction with 3 steps 1: sodium acetate; acetic acid; bromine / water / 2.5 h / 45 °C 2: N,N-dimethyl-formamide / 24 h / 50 °C / Molecular sieve 3: N,N-dimethyl-formamide / 6 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sodium acetate; acetic acid; bromine / water / 2.5 h / 45 °C 2: isopropyl alcohol / 24 h / 20 °C | ||
Multi-step reaction with 3 steps 1: sodium acetate; acetic acid; bromine / water / 2.5 h / 45 °C 2: N,N-dimethyl-formamide / 24 h / 50 °C / Molecular sieve 3: isopropyl alcohol / 24 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: sodium acetate; acetic acid; bromine / water / 2.5 h / 45 °C 2: N,N-dimethyl-formamide / 6 h / 20 °C 3: dihydrogen peroxide / N,N-dimethyl-formamide / 20 °C | ||
Multi-step reaction with 4 steps 1: sodium acetate; acetic acid; bromine / water / 2.5 h / 45 °C 2: N,N-dimethyl-formamide / 24 h / 50 °C / Molecular sieve 3: N,N-dimethyl-formamide / 6 h / 20 °C 4: dihydrogen peroxide / N,N-dimethyl-formamide / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: sodium acetate; acetic acid; bromine / water / 2.5 h / 45 °C 2: N,N-dimethyl-formamide / 6 h / 20 °C 3: acetic acid; potassium permanganate / 0.75 h / -5 °C 4: N,N-dimethyl-formamide / 24 h / 20 °C | ||
Multi-step reaction with 5 steps 1: sodium acetate; acetic acid; bromine / water / 2.5 h / 45 °C 2: N,N-dimethyl-formamide / 24 h / 50 °C / Molecular sieve 3: N,N-dimethyl-formamide / 6 h / 20 °C 4: acetic acid; potassium permanganate / 0.75 h / -5 °C 5: N,N-dimethyl-formamide / 24 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: sodium acetate; acetic acid; bromine / water / 2.5 h / 45 °C 2: N,N-dimethyl-formamide / 6 h / 20 °C 3: acetic acid; potassium permanganate / 0.75 h / -5 °C 4: N,N-dimethyl-formamide / 24 h / 20 °C 5: acetic acid; 10% PdO/BaSO4; hydrogen / propan-1-ol / 3 h / 20 °C / 759.83 Torr | ||
Multi-step reaction with 6 steps 1: sodium acetate; acetic acid; bromine / water / 2.5 h / 45 °C 2: N,N-dimethyl-formamide / 24 h / 50 °C / Molecular sieve 3: N,N-dimethyl-formamide / 6 h / 20 °C 4: acetic acid; potassium permanganate / 0.75 h / -5 °C 5: N,N-dimethyl-formamide / 24 h / 20 °C 6: acetic acid; 10% PdO/BaSO4; hydrogen / propan-1-ol / 3 h / 20 °C / 759.83 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: sodium acetate; acetic acid; bromine / water / 2.5 h / 45 °C 2.1: N,N-dimethyl-formamide / 6 h / 20 °C 3.1: acetic acid; potassium permanganate / 0.75 h / -5 °C 4.1: N,N-dimethyl-formamide / 24 h / 20 °C 5.1: potassium <i>tert</i>-butylate / 18 h / 20 °C 5.2: 1.5 h / -10 °C | ||
Multi-step reaction with 6 steps 1.1: sodium acetate; acetic acid; bromine / water / 2.5 h / 45 °C 2.1: N,N-dimethyl-formamide / 24 h / 50 °C / Molecular sieve 3.1: N,N-dimethyl-formamide / 6 h / 20 °C 4.1: acetic acid; potassium permanganate / 0.75 h / -5 °C 5.1: N,N-dimethyl-formamide / 24 h / 20 °C 6.1: potassium <i>tert</i>-butylate / 18 h / 20 °C 6.2: 1.5 h / -10 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: sodium acetate; acetic acid; bromine / water / 2.5 h / 45 °C 2: N,N-dimethyl-formamide / 6 h / 20 °C 3: acetic acid; potassium permanganate / 0.75 h / -5 °C 4: N,N-dimethyl-formamide / 24 h / 20 °C 5: potassium cyanide / ethanol / 96 h / 20 °C | ||
Multi-step reaction with 6 steps 1.1: sodium acetate; acetic acid; bromine / water / 2.5 h / 45 °C 2.1: N,N-dimethyl-formamide / 6 h / 20 °C 3.1: acetic acid; potassium permanganate / 0.75 h / -5 °C 4.1: N,N-dimethyl-formamide / 24 h / 20 °C 5.1: potassium <i>tert</i>-butylate / 18 h / 20 °C 5.2: 1.5 h / -10 °C 6.1: methanol; sodium hydroxide / methanol / 6 h / 20 °C | ||
Multi-step reaction with 6 steps 1: sodium acetate; acetic acid; bromine / water / 2.5 h / 45 °C 2: N,N-dimethyl-formamide / 24 h / 50 °C / Molecular sieve 3: N,N-dimethyl-formamide / 6 h / 20 °C 4: acetic acid; potassium permanganate / 0.75 h / -5 °C 5: N,N-dimethyl-formamide / 24 h / 20 °C 6: potassium cyanide / ethanol / 96 h / 20 °C |
Multi-step reaction with 7 steps 1.1: sodium acetate; acetic acid; bromine / water / 2.5 h / 45 °C 2.1: N,N-dimethyl-formamide / 24 h / 50 °C / Molecular sieve 3.1: N,N-dimethyl-formamide / 6 h / 20 °C 4.1: acetic acid; potassium permanganate / 0.75 h / -5 °C 5.1: N,N-dimethyl-formamide / 24 h / 20 °C 6.1: potassium <i>tert</i>-butylate / 18 h / 20 °C 6.2: 1.5 h / -10 °C 7.1: methanol; sodium hydroxide / methanol / 6 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
22%; 45% | With bromine; sodium acetate; acetic acid; In water; at 45℃; for 2.5h; | 6-Benzylamino-9-(beta-D-ribofuranosyl)purine (469.4 mg; 1.313 mmol) was suspended in 15 ml 1 M AcONa and 15 ml 1 M AcOH. Bromine water (12.7 ml) was added to suspension and mixture was heated for 2.5 h at 45 C. Excess bromine was eliminated by addition of solid NaHSO3 and then the mixture was neutralized by 10% NaOH and evaporated. Residue was shaken out with water and chloroform. Organic layer was separated, dried in MgSO4 and after filtration of desiccant evaporated to dryness. The residue was purified by column chromatography in CHCl3-MeOH-NH4OH (95:5:0.5). Yield 126.5 mg 6-benzylamino-8-bromo-9-(beta-D-ribofuranosyl)purine (22%), 42.2 mg starting material (9%), 205 mg 8-bromoadenosine (45%) and mixture of benzaldehyde and bromobenzaldehyde. Crystallization from CHCl3-hexan; mp: 98-100 C. MS ESI+: 436.2 [M+H+]. For C17H13BrN5O4 calculated 435.0542, found 436.0680 [M+H+]. 1H NMR (400 MHz; CDCl3) delta 3.75 (dd, J=2.7 Hz, 12.7 Hz, H5?), 3.90 (dd, J=2.4 Hz, 12.7 Hz, H5?), 4.20 (d, J=1.8 Hz, H4?), 4.39 (dd, J=1.8 Hz, 5.3 Hz, H3?), 4.81 (bs, -CH2-), 5.08 (dd, J=5.3 Hz, 7.2 Hz, H2?), 6.07 (d, J=7.2 Hz, H1?), 7.24 (m, H4-Ph), 7.31 (m, H3-Ph), 7.38 (m, H2-Ph), 8.19 (s, H2). MS ESI+ (8-bromoadenosine): 346.3 [M+H+]. GC: Rt (benzaldehyde)=321 s. MS EI (benzyldehyde): 105 (100%), 77 (25%). Rt (bromobenzyldehyde)=722 s. MS EI: 185 (100%), 155 (50%), 77 (45%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sodium acetate; acetic acid; bromine / water / 2.5 h / 45 °C 2: N,N-dimethyl-formamide / 24 h / 50 °C / Molecular sieve | ||
With bromine In aq. acetate buffer for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
32% | Stage #1: 1-N-benzyl-N<SUP>6</SUP>-acetyl-2',3',5'-tri-O-acetyladenosine With ammonia In methanol at 20℃; for 120h; Stage #2: With ammonium hydroxide at 20℃; for 168h; | Method B A solution of nucleoside 10b (100 mg, 0.19 mmol) in 7 M NH3 in MeOH (1.5 mL) was kept at r.t. for 5 days and then evaporated in vacuum. The residue was dissolved in 25% aqueous ammonia (5 mL), kept at r.t. during a week and then was evaporated in vacuum. The residue was diluted with brine (20 mL), and the product was extracted with ethylacetate (5 × 10 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to dryness. The residue was purified by column chromatography on silica gel (column diam. 10 mm, sorbent volume - 5 mL), using EtOH-CH2Cl2 gradient, increasing in polarity from CH2Cl2 toCH2Cl2:EtOH (9:1). The resulting product was recrystallized from 4.5 mL of EtOH-H2O (1:9). The precipitate was filtered and washed with cold water (2 × 2 mL). The pure product was dried in vacuum desiccator over P2O5 to give 5b as white crystals (21 mg, 32%); Rf = 0.32 (CH2Cl2 - EtOH, 95:5). 1HNMRand 13C NMR spectra were identical to those reported earlier.[23 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
149 mg | With ammonium hydroxide at 20℃; for 168h; | Method A To a solution of triacetyladenosine 1 (200 mg, 0.51 mmol) in DMF (2 mL) barium carbonate (246 mg, 1.25 mmol), potassium iodide (166 mg, 1 mmol) and benzyl bromide (0.119 mL, 1 mmol) were added, and the mixture was stirred at 65C for 24 hours. Then the mixture was cooled to r.t., diluted with ethyl acetate (20 mL) and filtered through Hyflo Super Cel (celite) from BaCO3. Celite was washed with ethyl acetate (2 × 10 mL). The combined filtrate was evaporated in vacuum to the volume ca. 2 mL. Then 25% aqueous ammonia (20 mL) was added, and the mixture was left to stay at r.t. during a week. The mixture was evaporated in vacuum, evaporated with EtOH (2 × 10 mL), and the product was crystallized from 4.5 mL of MeOH-H2O (1:8). The precipitate was filtered and washed with cold water (2 × 2 mL), and the resulting nucleoside 5b was dried in vacuum desiccator over P2O5 to give 116 mg of crystals. The residual nucleoside 5b was extracted from mother liquor with ethylacetate (2 × 20 mL), crystallized from 1.5mL ofMeOH-H2O(1:8) and dried in vacuum desiccator over P2O5 to give 33 mg of 5b. Yield of pure product - 149 mg (82% for two steps) as white crystals; mp 164-165C [Lit.[29,30] 167-168C]; Rf = 0.32 (CH2Cl2 -EtOH, 95:5). |
Multi-step reaction with 2 steps 1.1: pyridine / 24 h 2.1: ammonia / methanol / 120 h / 20 °C 2.2: 168 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With pyridine at 20℃; for 24h; | N6-Benzyl-5′-O-trityladenosine (1i) The solution of N6-benzyladenosine (70 mg, 0.1955 mmol) and trityl chloride (89 mg, 0.32 mmol)in pyridine (2 ml) was held at room temperature for 24 h. Ethanol (1ml) was then added to themixture and the mixture was evaporated in vacuum. The residue was diluted with ethyl acetate andwashed successively with 10% aqueous sodium bicarbonate (20 ml) and brine (2×20 ml). Theorganic layer was separated, dried over anhydrous sodium sulfate, filtered and evaporated invacuum. The residue was applied on chromatographic column with silica gel (5 ml). The productwas eluted with systems CH2Cl2 - EtOH-98:2 (75 ml) and CH2Cl2 - EtOH-95:5 (25 ml). Thefractions, containing the product, were collected and evaporated in vacuum to dryness. The residuewas dried on the vacuum pump for 1 h. Yield 76 mg (65%) as a white powder. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | With pyridine at 20℃; for 24h; | N6-Benzyl-5′-O-tert-butyldimethylsilyladenosine (1j) The solution of N6-benzyladenosine (70 mg, 0.1955 mmol) and tert-butyldimethylchlorosilane (34mg, 0.225 mmol) in pyridine (2 ml) was held at room temperature for 24 h. Ethanol (1ml) was thenadded to the mixture and the mixture was evaporated in vacuum. The residue was diluted with ethylacetate and washed successively with 10% aqueous sodium bicarbonate (20 ml) and brine (2×20ml). The organic layer was separated, dried over anhydrous sodium sulfate, filtered and evaporatedin vacuum. The residue was applied on chromatographic column with silica gel (5 ml). The productwas eluted with systems CH2Cl2 - EtOH-98:2 (25 ml), CH2Cl2 - EtOH-98:2 (25 ml) and CH2Cl2 -EtOH-95:5 (25 ml). The fractions, containing the product, were collected and evaporated in vacuumto dryness. The residue was dried on the vacuum pump for 1 h. Yield 81 mg (88%) as a white lightfoam. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With pyridine at 20℃; for 24h; | N6-Benzyl-5′-O-tert-butyldimethylsilyladenosine (1j) The solution of N6-benzyladenosine (70 mg, 0.1955 mmol) and tert-butyldimethylchlorosilane (34mg, 0.225 mmol) in pyridine (2 ml) was held at room temperature for 24 h. Ethanol (1ml) was thenadded to the mixture and the mixture was evaporated in vacuum. The residue was diluted with ethylacetate and washed successively with 10% aqueous sodium bicarbonate (20 ml) and brine (2×20ml). The organic layer was separated, dried over anhydrous sodium sulfate, filtered and evaporatedin vacuum. The residue was applied on chromatographic column with silica gel (5 ml). The productwas eluted with systems CH2Cl2 - EtOH-98:2 (25 ml), CH2Cl2 - EtOH-98:2 (25 ml) and CH2Cl2 -EtOH-95:5 (25 ml). The fractions, containing the product, were collected and evaporated in vacuumto dryness. The residue was dried on the vacuum pump for 1 h. Yield 81 mg (88%) as a white lightfoam. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: toluene-4-sulfonic acid / acetone / 16 h / 20 °C 2.1: triphenylphosphine / tetrahydrofuran / 0.17 h / 20 °C 3.1: dmap; di-<i>tert</i>-butyl dicarbonate / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere 4.1: ethylenediamine / ethanol / 6 h / 70 °C 5.1: magnesium methanolate / methanol / 3 h / 55 °C 5.2: 3 h / 20 °C | ||
Multi-step reaction with 6 steps 1.1: toluene-4-sulfonic acid / acetone / 16 h / 20 °C 2.1: triphenylphosphine / tetrahydrofuran / 0.17 h / 20 °C 3.1: dmap; di-<i>tert</i>-butyl dicarbonate / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere 4.1: ethylenediamine / ethanol / 6 h / 70 °C 5.1: magnesium methanolate / methanol / 3 h / 55 °C 5.2: 3 h / 20 °C 6.1: water; lithium hydroxide / tetrahydrofuran / 6 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: toluene-4-sulfonic acid / acetone / 16 h / 20 °C 2.1: triphenylphosphine / tetrahydrofuran / 0.17 h / 20 °C 3.1: dmap; di-<i>tert</i>-butyl dicarbonate / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere 4.1: ethylenediamine / ethanol / 6 h / 70 °C 5.1: magnesium methanolate / methanol / 3 h / 55 °C 5.2: 3 h / 20 °C 6.1: trifluoroacetic acid / dichloromethane / 16 h / 0 °C | ||
Multi-step reaction with 7 steps 1.1: toluene-4-sulfonic acid / acetone / 16 h / 20 °C 2.1: triphenylphosphine / tetrahydrofuran / 0.17 h / 20 °C 3.1: dmap; di-<i>tert</i>-butyl dicarbonate / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere 4.1: ethylenediamine / ethanol / 6 h / 70 °C 5.1: magnesium methanolate / methanol / 3 h / 55 °C 5.2: 3 h / 20 °C 6.1: water; lithium hydroxide / tetrahydrofuran / 6 h / 20 °C 7.1: trifluoroacetic acid / dichloromethane / 16 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; trimethyl phosphite; trichlorophosphate / Inert atmosphere; Cooling 2.1: tributyl-amine / ethanol; water / pH 7 - 8 2.2: Inert atmosphere; Cooling 2.3: 3407 / 1 h / 20 °C / pH 7.4 - 7.6 / Cooling; Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | Stage #1: uridine With magnesium(II) chloride hexahydrate; recombinant E. coli uridine phosphorylase In aq. phosphate buffer at 20℃; for 72h; Stage #2: 6-benzylaminopurine In aq. phosphate buffer at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | With recombinant E. coli purine nucleoside phosphorylase In aq. phosphate buffer at 40℃; for 26h; | N6-Benzyladenosine To a heterogeneous reaction mixture containing guanosine (425 mg, 1.5 mmol) and N6-benzyladenine (225 mg,1 mmol) in 140 mL of 5.0 mM K-phosphate buffer (pH 7.0) was added E. coli PNP (140 IU) and the mixture was gently stirred at 40 °C for 20 h(some quantity of the starting heterocyclic base remained in the reaction mixture according to TLC). Then, guanosine (0.14 g, 0.5 mmol) wasadded and the heating continued for 6 h and the reaction mixture was left overnight at 4 °C. The solution was decanted from the precipitateformed and evaporated to dryness, the residue was mixed with one tee spoon of SiO2 and put on the top of a standard column (2 × 22 cm) packedin DCE/MeOH 95:5 (vol). Elution with the same mixture of solvents gave 20 mg of N6-benzyladenine and its riboside (0.22 g, yield 67%; purity99.2% according to HPLC) |
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Code | Phrase |
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Code | Phrase |
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Response | |
Code | Phrase |
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P378 | |
P380 | Evacuate area. |
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Storage | |
Code | Phrase |
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P402 | Store in a dry place. |
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Disposal | |
Code | Phrase |
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Physical hazards | |
Code | Phrase |
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H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
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Health hazards | |
Code | Phrase |
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H311 | Toxic in contact with skin |
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H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
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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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