TY - JOUR
T1 - Preparation of 6-O-alkylcelluloses
AU - Kondo, Tetsuo
PY - 1993/1/15
Y1 - 1993/1/15
N2 - Cellulose derivatives specifically substituted at the primary hydroxyl groups, 6-O-alkylcelluloses, were prepared from 6-O-tritylcellulose (trityl = triphenylmethyl). In the preferred procedure, the 6-O-tritylcellulose was first completely allylated in dimethyl sulfoxide (Me2SO), and subsequently detritylated with hydrogen chloride to yield 2,3-di-O-allylcellulose. This product was isomerized into 2,3-di-O-(1-propenyl)cellulose with potassium tert-butoxide in Me2SO. The polymer thus prepared was then alkylated completely with methyl or ethyl iodide in Me2SO containing a trace of water. The alkylated polymer was finally treated with 0.1 M HCl in aqueous 90% methanol at room temperature to remove the 1-propenyl groups. The products were shown by Fourier-transform infrared spectroscopy, 13C nuclear magnetic resonance spectroscopy, and gas-liquid chromatographic analysis to be uniformly substituted at the 6 position.
AB - Cellulose derivatives specifically substituted at the primary hydroxyl groups, 6-O-alkylcelluloses, were prepared from 6-O-tritylcellulose (trityl = triphenylmethyl). In the preferred procedure, the 6-O-tritylcellulose was first completely allylated in dimethyl sulfoxide (Me2SO), and subsequently detritylated with hydrogen chloride to yield 2,3-di-O-allylcellulose. This product was isomerized into 2,3-di-O-(1-propenyl)cellulose with potassium tert-butoxide in Me2SO. The polymer thus prepared was then alkylated completely with methyl or ethyl iodide in Me2SO containing a trace of water. The alkylated polymer was finally treated with 0.1 M HCl in aqueous 90% methanol at room temperature to remove the 1-propenyl groups. The products were shown by Fourier-transform infrared spectroscopy, 13C nuclear magnetic resonance spectroscopy, and gas-liquid chromatographic analysis to be uniformly substituted at the 6 position.
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U2 - 10.1016/0008-6215(93)87015-K
DO - 10.1016/0008-6215(93)87015-K
M3 - Article
AN - SCOPUS:0027449945
VL - 238
SP - 231
EP - 240
JO - Carbohydrate Research
JF - Carbohydrate Research
SN - 0008-6215
IS - C
ER -