Synthesis of mono-O-(2-diethylaminoethyl)-d-glucoses and distribution of substituent groups in O-(2-diethylaminoethyl)cellulose

Abstract

O-(2-Diethylaminoethyl)cellulose (degree of substitution 0.048) was prepared by reacting cotton cellulose, in the form of fabric, with 2-diethylaminoethyl chloride in the presence of excess sodium hydroxide at room temperature. The modified cellulose was hydrolyzed and the substituted glucoses were identified by chromatographic comparison with authentic 2-O-, 3-O-, and 6-O-(2-diethylaminoethyl)-d-glucoses in the form of their trimethylsilyl ethers. Syntheses of authentic 2-O-, 3-O-, and 6-O-(2-diethylaminoethyl)-d-glucoses are described. The relative distribution of 2-diethylaminoethyl groups among the 2-O-, 3-O-, and 6-O-positions of the d-glucopyranosyl residue of cotton cellulose was found to be 1.27:0.35:1.00.