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Chemical Structure| 63273-48-3 Chemical Structure| 63273-48-3

Structure of 63273-48-3

Chemical Structure| 63273-48-3

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Product Details of [ 63273-48-3 ]

CAS No. :63273-48-3
Formula : C13H15NO3
M.W : 233.27
SMILES Code : O=C1N(C(C2=CC=CC=C21)=O)CCCCCO
MDL No. :MFCD09923385

Safety of [ 63273-48-3 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H319
Precautionary Statements:P264-P280-P305+P351+P338-P337+P313

Application In Synthesis of [ 63273-48-3 ]

* 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.

  • Downstream synthetic route of [ 63273-48-3 ]

[ 63273-48-3 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 38222-83-2 ]
  • [ 63273-48-3 ]
  • [ 149831-83-4 ]
  • [ 149831-91-4 ]
  • [ 149831-92-5 ]
YieldReaction ConditionsOperation in experiment
78% With trifluoromethylsulfonic anhydride; In dichloromethane; A stirred solution of 5-phthalimido-1-pentanol (III-33) (39.1 mg, 0.168 mmol) and <strong>[38222-83-2]2,6-di-tert-butyl-4-methylpyridine</strong> (34.5 mg, 0.168 mmol) in dry dichloromethane (1.5 ml) was treated with triflic anhydride (28.3 ml, 0.168 mmol). After 10 min at room temperature, the mixture was diluted with water (25 ml) and extracted with dichloromethane (2*50 ml). The combined extracts were washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo, affording a yellow solid which was used without purification in the next reaction. Sodium hydride (60percent dispersion in oil, 51 mg, 1.3 mmol) was added to a solution of alcohol III-44 (150 mg, 0.240 mmol), 5-phthalimidopentyl triflate (1.37 mmol), and <strong>[38222-83-2]2,6-di-tert-butyl-4-methylpyridine</strong> (282 mg, 1.39 mmol), in dichloromethane (1.5 ml) at 0° C. The reaction mixture was stirred for 48 h at room temperature, quenched with saturated aqueous ammonium chloride, and extracted with dichloromethane, and the organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (20percent ethyl acetate/petroleum ether) gave III-45 (158 mg, 78percent yield) as a colorless oil: [alpha]D25 -2.5° (c 0.36, acetonitrile); UV (2.14*10-4 M, acetonitrile) lambdamax 283.6 (epsilon710), 242.4 (808) nm; IR (CHCl3) 2940 (m), 2860 (m), 1775 (m), 1715 (s), 1450 (m), 1400 (s), 1370 (s), 1175 (m), 1120 (s), 1090 (s), 1050 (s), 745 (m), 720 (s), 700 (m) cm-1; 1 H NMR (500 MHz, CDCl3) delta7.96 (d, J=8.3 Hz, 1H), 7.84-7.80 (m, 4H), 7.69-7.64 (m, 2H), 7.50-7.17 (m, 12H), 4.69 (d, J=11.0 Hz, 1H), 4.67 (s, 2H), 4.64 (d, J=11.0 Hz, 1H), 4.36 (d, J=7.7 Hz, 1H), 4.21-4.17 (m, 1H), 3.86-3.81 (m, 1H), 3.66 (t, J=7.3 Hz, 2H), 3.60-3.39 (m, 6H), 3.28 (dd, J=7.8, 8.8 Hz, 1H), 3.00 (t, J=6.7 Hz, 2H), 2.12 (dd, J=5.4, 12.2 Hz, 1H), 1.71-1.58 (m, 5H), 1.47-1.36 (m, 3H); 13 C NMR (125 MHz, CDCl3) delta168.37, 138.61, 138.31, 135.19, 133.83, 133.56, 132.13, 131.03, 129.11, 128.31, 128.19, 127.96, 127.63, 127.51, 127.44, 126.65, 124.68, 123.51, 123.12, 119.78, 119.49, 113.70, 103.85, 82.83, 78.23, 74.90, 73.10, 72.16, 71.39, 70.95, 68.68, 37.86, 33.94, 29.67, 29.11, 28.36, 25.75, 23.41; high resolution mass spectrum (FAB, m-nitrobenzyl alcohol) m/z 865.3201 [(M+Na)+; calcd for C49 H50 N2 O9 SNa: 865.3134].
  • 2
  • [ 38222-83-2 ]
  • [ 2508-29-4 ]
  • [ 22509-74-6 ]
  • [ 63273-48-3 ]
  • [ 149831-83-4 ]
YieldReaction ConditionsOperation in experiment
With trifluoromethylsulfonic anhydride; In dichloromethane; benzene; A. 5-Phthalimido-1-pentyl triflate (15). To a solution of 5-aminopentanol (42.7 mmol) in benzene (100 mL) is added N-carbethoxyphthalimide (10.3 g, 47.0 mmol). The solution is stirred at room temperature for 5 h. The solvent is removed in vacuo to provide an oil, which is purified by flash chromatography. To a solution of 5-phthalimido-1-pentanol (22.2 mmol) in dry dichloromethane (50 mL) is added <strong>[38222-83-2]2,6-di-tert-butyl-4-methylpyridine</strong> (4.6 g, 22.2 mmol) and triflic anhydride (3.7 mL, 22.2 mmol) at 0° C. The reaction is stirred at room temperature for 20 min, poured into water, and extracted with dichloromethane. The combined extracts are dried over anhydrous sodium sulfate and concentrated in vacuo and to afford 5-phthalimido-1-pentyl triflate (15) which is used without further purification.
  • 3
  • [ 38222-83-2 ]
  • [ 63273-48-3 ]
  • [ 149831-83-4 ]
YieldReaction ConditionsOperation in experiment
With trifluoromethylsulfonic anhydride; In dichloromethane; L. 5-Phthalimido-1-O-trifluoromethanesulfonylpentanol To a solution of 5-phthalimido-1-pentanol (39.1 mg, 0.168 mmol) in dry dichloromethane (1.5 mL) was added <strong>[38222-83-2]2,6-di-tert-butyl-4-methylpyridine</strong> (34.5 mg, 0.168 mmol) followed by triflic anhydride (28.3 mug, 0.168 mmol). The solution was stirred at room temperature for 10 minutes. The reaction was poured into water (25 mL) and extracted with dichloromethane (2*50 mL). The organic layer was washed with a saturated sodium chloride solution and dried with anhydrous sodium sulfate. The solvents were removed under reduced pressure to yield a pale yellow solid which was used immediately without further purification.
  • 4
  • [ 38222-83-2 ]
  • [ 63273-48-3 ]
  • [ 149831-84-5 ]
YieldReaction ConditionsOperation in experiment
86% With trifluoromethylsulfonic anhydride; In dichloromethane; A stirred solution of 5-phthalimido-1-pentanol (III-33) (1.32 g, 4.67 mmol) and <strong>[38222-83-2]2,6-di-tert-butyl-4-methylpyridine</strong> (0.960 g, 4.67 mmol) in dry dichloromethane (10 ml) was treated with triflic anhydride (0.784 ml, 4.67 mmol). After 10 min at room temperature, the mixture was diluted with water (100 ml) and extracted with dichloromethane (2*200 ml). The combined extracts were washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo, affording a yellow solid which was used without purification in the next reaction. Sodium hydride (60percent dispersion in oil, 0.20 g, 5.06 mmol) was added to a solution of alcohol III-32 (1.27 g, 3.89 mmol), 5-phthalimdopentyl triflate (4.67 mmol), and 15-crown-5 (20 mg, 2.3 mol percent), in dichloromethane (100 ml) at 0° C. After stirring for 24 h at room temperature, the mixture was poured into water. The aqueous layer was extracted with dichloromethane (3*50 ml) and the combined extracts were washed with water, dried over magnesium sulfate and concentrated in vacuo. Flash chromatography (3percent ether/dichloromethane) provided III-34 (1.82 g, 86percent yield) as a colorless oil: [alpha]D25 -8.2° (c 0.70, CHCl3); IR (CHCl3) 3080 (w), 3020 (m), 3009 (m), 2959 (m), 2880 (m), 1780 (m), 1719 (s), 1652 (m), 1500 (w), 1470 (w), 1457 (m), 1440 (m), 1400 (s), 1365 (m), 1235 (m), 1110 (br, s), 1058 (br, s), 908 (w), 692 (m), cm-1; 1 H NMR (500 MHz, CDCl3) delta7.80 (m, 2H), 7.68 (m, 2H), 7.25-7.34 (m, 10H), 6.38, (dd, J=6.1, 1.2 Hz, 1H), 4.84 (m, 2H), 4.66 (d, J=11.4 Hz, 1H), 4.63 (d, J=11.7 Hz, 1H), 4.55 (d, J=11.7 Hz, 1H), 4.19 (m, 1H), 4.00 (m, 1H), 3.81 (dd, J=8.7, 6.2 Hz, 1H), 3.64-3.74 (m, 4H), 3.40-3.50 (m, 2H), 1.60-1.70 (m, 4H), 1.40 (m, 2H); 13 C NMR (62.9 MHz, CDCl3) delta168.4, 144.8, 138.4, 138.3, 133.9, 132.2, 128.4, 127.9, 127.8, 127.6, 123.2, 99.9, 76.8, 75.8, 74.5, 73.8, 71.4, 70.5, 69.2, 37.9, 29.2, 28.5, 23.5; high resolution mass spectrum (Cl, NH3) m/z 541.2483 (M+; calcd for C33 H35 NO6: 541.2464).
  • 5
  • [ 38222-83-2 ]
  • 15-crown-S [ No CAS ]
  • [ 63273-48-3 ]
  • [ 149831-84-5 ]
YieldReaction ConditionsOperation in experiment
86% With trifluoromethylsulfonic anhydride; In dichloromethane; AG. 3,4-Di-O-Benzyl-6-O-(5-phthalimidopentyl)-D-glucal (III-34) 5-Phthalimidopentyl triflate was prepared as follows: A stirred solution of 5-phthalimido-1-pentanol (III-33) (1.32 g, 4.67 mmol) and <strong>[38222-83-2]2,6-di-tert-butyl-4-methylpyridine</strong> (0.960 g, 4.67 mmol) in dry dichloromethane (10 ml) was treated with triflic anhydride (0.784 ml, 4.67 mmol). After 10 min at room temperature, the mixture was diluted with water (100 ml) and extracted with dichloromethane (2*200 ml). The combined extracts were washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo, affording a yellow solid which was used without purification in the next reaction. Sodium hydride (60percent dispersion in oil, 0.20 g, 5.06 mmol) was added to a solution of alcohol III-32 (1.27 g, 3.89 mmol), 5-phthalimdopentyl triflate (4.67 mmol), and 15-crown-S (20 mg, 2.3 mol percent), in dichloromethane (100 ml) at 0° C. After stirring for 24 h at room temperature, the mixture was poured into water. The aqueous layer was extracted with dichloromethane (3*50 ml) and the combined extracts were washed with water, dried over magnesium sulfate and concentrated in vacuo. Flash chromatography (3percent ether/dichloromethane) provided III-34 (1.82 g, 86percent yield) as a colorless oil: [alpha]D25 -8.20 (c 0.70, CHCl3); IR (CHCl3) 3080 (w), 3020 (m), 3009 (m), 2959 (m), 2880 (m), 1780 (m), 1719 (s), 1652 (m), 1500 (w), 1470 (w), 1457 (m), 1440 (m), 1400 (s), 1365 (m), 1235 (m), 1110 (br, s), 1058 (br, s), 908 (w), 692 (m), cm-1; 1 H NMR (500 MHz, CDCl3) delta7.80 (m, 2 H), 7.68 (m, 2 H), 7.25-7.34 (m, 10 H), 6.38, (dd, J=6.1, 1.2 Hz, 1 H), 4.84 (m, 2 H), 4.66 (d, J=11.4 Hz, 1 H), 4.63 (d, J=11.7 Hz, 1 H), 4.55 (d, J=11.7 Hz, 1 H), 4.19 (m, 1 H), 4.00 (m, 1 H), 3.81 (dd, J=8.7, 6.2 Hz, 1 H), 3.64-3.74 (m, 4 H), 3.40-3.50 (m, 2 H), 1.60-1.70 (m, 4 H), 1.40 (m, 2 H); 13 C NMR (62.9 MHz, CDCl3) delta168.4, 144.8, 138.4, 138.3, 133.9, 132.2, 128.4, 127.9, 127.8, 127.6, 123.2, 99.9, 76.8, 75.8, 74.5, 73.8, 71.4, 70.5, 69.2, 37.9, 29.2, 28.5, 23.5; high resolution mass spectrum (Cl, NH3) m/z 541.2483 (M+; calcd for C33 H35 NO6: 541.2464).
 

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