1-Phenyl-2,5,8,11,14,17,20,23-octaoxapentacosan-25-ol

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of tetrahydrofuran (140 mL) containing sodium hydride (0.43 g, 18 mmol) was added dropwise a solution of monodispersed tetraethylene glycol (3.5 g, 18 mmol) in tetrahydrofuran (10 mL) and the reaction mixture was stirred for 1 h. Then mesylate of monodispersed tetraethylene glycol monobenzylether 24 (6.0 g, 16.5 mmol) dissolved in tetrahydrofuran (10 mL) was added dropwise and the reaction mixture was stirred overnight. The crude reaction mixture was filtered through Celite (washed; CH2Cl2, 250 mL) and the filtrate was washed H2O, dried MgSO4, and evaporated to dryness. The resultant oil was chromatographed (silica, ethyl acetate/methanol, 10:1) and chromatographed (silica, chloroform/methanol, 25:1) to afford the monodispersed compound 25 as a clear oil (2.62 g, 34% yield). was added dropwise the reaction mixture was stirred overnight The crude reaction mixture was filtered through Celite (washed; CH2Cl2, 250 mL) the filtrate was washed H2O, dried MgSO4 evaporated to dryness The resultant oil was chromatographed (silica, ethyl acetate/methanol, 10:1) chromatographed (silica, chloroform/methanol, 25:1)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of tetrahydrofuran (140 mL) containing sodium hydride (0.43 g, 18 mmol) was added dropwise a solution of monodispersed tetraethylene glycol (3.5 g, 18 mmol) in tetrahydrofuran (10 mL) and the reaction mixture was stirred for 1 h. Then mesylate of monodispersed tetraethylene glycol monobenzylether 24 (6.0 g, 16.5 mmol) dissolved in tetrahydrofuran (10 mL) was added dropwise and the reaction mixture was stirred overnight. The crude reaction mixture was filtered through Celite (washed, CH2Cl2, 250 mL) and the filtrate was washed H2O, dried MgSO4, and evaporated to dryness. The resultant oil was chromatographed (silica, ethyl acetate/methanol, 10:1) and chromatographed (silica, chloroform/methanol, 25:1) to afford the monodispersed compound 25 as a clear oil (2.62 g, 34% yield). was added dropwise the reaction mixture was stirred overnight The crude reaction mixture was filtered through Celite (washed, CH2Cl2, 250 mL) the filtrate was washed H2O, dried MgSO4 evaporated to dryness The resultant oil was chromatographed (silica, ethyl acetate/methanol, 10:1) chromatographed (silica, chloroform/methanol, 25:1)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of tetrahydrofuran (140 mL) containing sodium hydride (0.43 g, 18 mmol) was added dropwise a solution of monodispersed tetraethylene glycol (3.5 g, 18 mmol) in tetrahydrofuran (10 mL) and the reaction mixture was stirred for 1 h. Then mesylate of monodispersed tetraethylene glycol monobenzylether 24 (6.0 g, 16.5 mmol) dissolved in tetrahydrofuran (10 mL) was added dropwise and the reaction mixture was stirred overnight. The crude reaction mixture was filtered through Celite (washed, CH2Cl2, 250 mL) and the filtrate was washed H2O, dried MgSO4, and evaporated to dryness. The resultant oil was chromatographed (silica, ethyl acetate/methanol, 10:1) and chromatographed (silica, chloroform/methanol, 25:1) to afford the monodispersed compound 25 as a clear oil (2.62 g, 34% yield). was added dropwise the reaction mixture was stirred overnight The crude reaction mixture was filtered through Celite (washed, CH2Cl2, 250 mL) the filtrate was washed H2O, dried MgSO4 evaporated to dryness The resultant oil was chromatographed (silica, ethyl acetate/methanol, 10:1) chromatographed (silica, chloroform/methanol, 25:1)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of tetrahydrofuran (140 mL) containing sodium hydride (0.43 g, 18 mmol) was added dropwise a solution of monodispersed tetraethylene glycol (3.5 g, 18 mmol) in tetrahydrofuran (10 mL) and the reaction mixture was stirred for 1 h. Then mesylate of monodispersed tetraethylene glycol monobenzylether 24 (6.0 g, 16.5 mmol) dissolved in tetrahydrofuran (10 mL) was added dropwise and the reaction mixture was stirred overnight. The crude reaction mixture was filtered through Celite (washed, CH2Cl2, 250 mL) and the filtrate was washed H2O, dried MgSO4, and evaporated to dryness. The resultant oil was chromatographed (silica, ethyl acetate/methanol, 10:1) and chromatographed (silica, chloroform/methanol, 25:1) to afford the monodispersed compound 25 as a clear oil (2.62 g, 34% yield). was added dropwise the reaction mixture was stirred overnight The crude reaction mixture was filtered through Celite (washed, CH2Cl2, 250 mL) the filtrate was washed H2O, dried MgSO4 evaporated to dryness The resultant oil was chromatographed (silica, ethyl acetate/methanol, 10:1) chromatographed (silica, chloroform/methanol, 25:1)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of tetrahydrofuran (140 mL) containing sodium hydride (0.43 g, 18 mmol) was added dropwise a solution of monodispersed tetraethylene glycol (3.5 g, 18 mmol) in tetrahydrofuran (10 mL) and the reaction mixture was stirred for 1 h. Then mesylate of monodispersed tetraethylene glycol monobenzylether 24 (6.0 g, 16.5 mmol) dissolved in tetrahydrofuran (10 mL) was added dropwise and the reaction mixture was stirred overnight. The crude reaction mixture was filtered through Celite (washed, CH2Cl2, 250 mL) and the filtrate was washed H2O, dried MgSO4, and evaporated to dryness. The resultant oil was chromatographed (silica, ethyl acetate/methanol, 10:1) and chromatographed (silica, chloroform/methanol, 25:1) to afford the monodispersed compound 25 as a clear oil (2.62 g, 34% yield). was added dropwise the reaction mixture was stirred overnight The crude reaction mixture was filtered through Celite (washed, CH2Cl2, 250 mL) the filtrate was washed H2O, dried MgSO4 evaporated to dryness The resultant oil was chromatographed (silica, ethyl acetate/methanol, 10:1) chromatographed (silica, chloroform/methanol, 25:1)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of tetrahydrofuran (140 mL) containing sodium hydride (0.43 g, 18 mmol) was added dropwise a solution of non-polydispersed tetraethylene glycol (3.5 g, 18 mmol) in tetrahydrofuran (10 mL) and the reaction mixture was stirred for 1 h. Then mesylate of non-polydispersed tetraethylene glycol monobenzylether 40 (6.0 g, 16.5 mmol) dissolved in tetrahydrofuran (10 mL) was added dropwise and the reaction mixture was stirred overnight. The crude reaction mixture was filtered through Celite (washed, CH2Cl2, 250 mL) and the filtrate was washed H2O, dried MgSO4, and evaporated to dryness. The resultant oil was chromatographed (silica, ethyl acetate/methanol, 10:1) and chromatographed (silica, chloroform/methanol, 25:1) to afford the non-polydispersed title compound as a clear oil (2.62 g, 34% yield). was added dropwise the reaction mixture was stirred overnight The crude reaction mixture was filtered through Celite (washed, CH2Cl2, 250 mL) the filtrate was washed H2O, dried MgSO4 evaporated to dryness The resultant oil was chromatographed (silica, ethyl acetate/methanol, 10:1) chromatographed (silica, chloroform/methanol, 25:1)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of tetrahydrofuran (140 mL) containing sodium hydride (0.43 g, 18 mmol) was added dropwise a solution of non-polydispersed tetraethylene glycol (3.5 g, 18 mmol) in tetrahydrofuran (10 mL) and the reaction mixture was stirred for 1 h. Then mesylate of non-polydispersed tetraethylene glycol monobenzylether 40 (6.0 g, 16.5 mmol) dissolved in tetrahydrofuran (10 mL) was added dropwise and the reaction mixture was stirred overnight. The crude reaction mixture was filtered through Celite (washed, CH2Cl2, 250 mL) and the filtrate was washed H2O, dried MgSO4, and evaporated to dryness. The resultant oil was chromatographed (silica, ethyl acetate/methanol, 10:1) and chromatographed (silica, chloroform/methanol, 25:1) to afford the non-polydispersed title compound as a clear oil (2.62 g, 34% yield). was added dropwise the reaction mixture was stirred overnight The crude reaction mixture was filtered through Celite (washed, CH2Cl2, 250 mL) the filtrate was washed H2O, dried MgSO4 evaporated to dryness The resultant oil was chromatographed (silica, ethyl acetate/methanol, 10:1) chromatographed (silica, chloroform/methanol, 25:1)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of tetrahydrofuran (140 mL) containing sodium hydride (0.43 g, 18 mmol) was added dropwise a solution of non-polydispersed tetraethylene glycol (3.5 g, 18 mmol) in tetrahydrofuran (10 mL) and the reaction mixture was stirred for 1 h. Then mesylate of non-polydispersed tetraethylene glycol monobenzylether 40 (6.0 g, 16.5 mmol) dissolved in tetrahydrofuran (10 mL) was added dropwise and the reaction mixture was stirred overnight. The crude reaction mixture was filtered through Celite (washed, CH2Cl2, 250 mL) and the filtrate was washed H2O, dried MgSO4, and evaporated to dryness. The resultant oil was chromatographed (silica, ethyl acetate/methanol, 10:1) and chromatographed (silica, chloroform/methanol, 25:1) to afford the non-polydispersed title compound as a clear oil (2.62 g, 34% yield). was added dropwise the reaction mixture was stirred overnight The crude reaction mixture was filtered through Celite (washed, CH2Cl2, 250 mL) the filtrate was washed H2O, dried MgSO4 evaporated to dryness The resultant oil was chromatographed (silica, ethyl acetate/methanol, 10:1) chromatographed (silica, chloroform/methanol, 25:1)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of tetrahydrofuran (140 mL) containing sodium hydride (0.43 g, 18 mmol) was added dropwise a solution of non-polydispersed tetraethylene glycol (3.5 g, 18 mmol) in tetrahydrofuran (10 mL) and the reaction mixture was stirred for 1 h. Then mesylate of non-polydispersed tetraethylene glycol monobenzylether 40 (6.0 g, 16.5 mmol) dissolved in tetrahydrofuran (10 mL) was added dropwise and the reaction mixture was stirred overnight. The crude reaction mixture was filtered through Celite (washed, CH2Cl2, 250 mL) and the filtrate was washed H2O, dried MgSO4, and evaporated to dryness. The resultant oil was chromatographed (silica, ethyl acetate/methanol, 10:1) and chromatographed (silica, chloroform/methanol, 25:1) to afford the non-polydispersed title compound as a clear oil (2.62 g, 34% yield). was added dropwise the reaction mixture was stirred overnight The crude reaction mixture was filtered through Celite (washed, CH2Cl2, 250 mL) the filtrate was washed H2O, dried MgSO4 evaporated to dryness The resultant oil was chromatographed (silica, ethyl acetate/methanol, 10:1) chromatographed (silica, chloroform/methanol, 25:1)

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of tetrahydrofuran (140 mL) containing sodium hydride (0.43 g, 18 mmol) was added dropwise a solution of non-polydispersed tetraethylene glycol (3.5 g, 18 mmol) in tetrahydrofuran (10 mL) and the reaction mixture was stirred for 1 h. Then mesylate of non-polydispersed tetraethylene glycol monobenzylether 40 (6.0 g, 16.5 mmol) dissolved in tetrahydrofuran (10 mL) was added dropwise and the reaction mixture was stirred overnight. The crude reaction mixture was filtered through Celite (washed, CH2Cl2, 250 mL) and the filtrate was washed H2O, dried MgSO4, and evaporated to dryness. The resultant oil was chromatographed (silica, ethyl acetate/methanol, 10:1) and chromatographed (silica, chloroform/methanol, 25:1) to afford the non-polydispersed title compound as a clear oil (2.62 g, 34% yield). was added dropwise the reaction mixture was stirred overnight The crude reaction mixture was filtered through Celite (washed, CH2Cl2, 250 mL) the filtrate was washed H2O, dried MgSO4 evaporated to dryness The resultant oil was chromatographed (silica, ethyl acetate/methanol, 10:1) chromatographed (silica, chloroform/methanol, 25:1)