2006
DOI: 10.1016/j.tet.2006.09.089
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Synthesis of calixarene–cyclodextrin coupling products

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Cited by 39 publications
(21 citation statements)
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“…Synthesis of azobenzene-bridgedb is(permethyl-b-CD): 4,4'-Dipropargyloxyazobenzene [16] (0.2 mmol, 58 mg) was added to as tirred solution of 6-deoxy-6-azide-permethyl-b-CD [17] (720 mg,0.5 mmol) in DMF (dimethylformamide;50mL), to which CuI (0.5 mmol, 95 mg) was added under argon at room temperature.The mixture was stirred overnight at 75 8 8C. After cooling to room temperature,t he mixture was filtered to remove any insoluble copper salt, and the filtrate was evaporatedu nder reduced pressure to remove excess DMF.T he residue was purified by silica gel column chromatography using chloroform-methanol solution (v/v = 50:1) as elutent to give azobenzene-bridged bis(permethyl-b-CD) (71 %) as orange foam (yield 71 %).…”
Section: Methodsmentioning
confidence: 99%
“…Synthesis of azobenzene-bridgedb is(permethyl-b-CD): 4,4'-Dipropargyloxyazobenzene [16] (0.2 mmol, 58 mg) was added to as tirred solution of 6-deoxy-6-azide-permethyl-b-CD [17] (720 mg,0.5 mmol) in DMF (dimethylformamide;50mL), to which CuI (0.5 mmol, 95 mg) was added under argon at room temperature.The mixture was stirred overnight at 75 8 8C. After cooling to room temperature,t he mixture was filtered to remove any insoluble copper salt, and the filtrate was evaporatedu nder reduced pressure to remove excess DMF.T he residue was purified by silica gel column chromatography using chloroform-methanol solution (v/v = 50:1) as elutent to give azobenzene-bridged bis(permethyl-b-CD) (71 %) as orange foam (yield 71 %).…”
Section: Methodsmentioning
confidence: 99%
“…b-CD was recrystallized twice from water and dried in vacuo at 90°C for 24 h. Mono[6-O-(p-toluenesulfonyl)]-b-CD (7), 16 mono-6-deoxy-6-(8-oxymethylquinolino)-b-CD (2), 17 and mono-6-deoxyl-6-azidob-CD (8) 7 were prepared according to the reported methods. Crude DMF was stirring in CaH 2 for three days and then distilled under reduced pressure prior to use.…”
Section: Generalmentioning
confidence: 99%
“…The methylated β-CD-N 3 was synthesized in a 3 step procedure starting from β-CD which was first converted via the 6- O -tosylate to β-CD-N 3 following the procedures of Hocquelet et al who also described the permethylated β-CD-N 3 [ 39 ]. Furthermore, we headed for the regioselective 2,6-dimethylated product.…”
Section: Resultsmentioning
confidence: 99%