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Reaction of methyl 4,6-O-benzylidene-β-D-glucopyranoside 2,3-bis-chlorosulphato and 6-O-trityl-cellulose 2,3-bis-chlorosulphate with dimethylamine
R. G. Krylova, A. S. Shashkov, A. I. Usov
A. D. Zelinsky Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow
Abstract: 6-O-Trityl-cellulose 2,3-bis-chlorosulphate was prepared by treatment of 6-O-trityl-cellulose with sulphuryl chloride in chloroform at -50 to -70°C or in toluene at 20°C. Its reaction with dimethylamine and subsequent detritylation afforded cellulose dimethylamidosulphate having DS ca. 0,6. According to 13C NMR spectral data, the di-methylamidosulphate groups substitute mainly position 2 of the glucopyranoside residues in the polymer. The model methyl 4,6-O-benzylidene-β-D-glucopyranoside 2,3-bis-chlorosulphate was transformed under similar conditions into the corresponding 2- and 3-dimethylamidosulphates isolated in approximately equal amounts. Their structure were elucidated by NMR spectroscopy and by mass-spectrometry of acetylated derivatives
Russian Journal of Bioorganic Chemistry 1991, 17 (5):702-709