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It has been found that 2-O-(2-hydroxyethyl)-D-glucopyranose is partially converted to 1,2-O-ethylene-α-D-glucofuranose, 1,2-O-ethylene-α-D-glucopyranose, and 1,2-O-ethylene-β-D-glucopyranose when heated in dilute acid solution. The ratio of the furanose derivative to the pyranose derivatives is dependent upon the concentration of the acid (3, 5). The three inner glucosides of 2-O-(2-hydroxyethyl)-D-glucose have been characterized by gas-liquid chromatography. The interrelationship of 2-O-(2-hydroxyethyl)-D-glucose and its inner glucosides is also reported.

O-(2-Aminoethyl)cellulose (degree of substitution 0.14), prepared by reaction of sodium 2-aminoethyl sulfate with cotton fabric, was hydrolyzed to glucose and mono-O-(2-aminoethyl)-D-glucopyranoses which were identified by gas–liquid chromatography (g.l.c.). Complications arise from reactions between the functional group at C-1 of the glucose unit and the amine function of a substituent. The distribution of 2-aminoethyl substituents in the 3-O- and 6-O-positions of the D-glucopyranosyl units of cotton cellulose was estimated to be 0.20:1.00 from direct analysis of the hydrolyzate of O-(2-aminoethyl)cellulose, but the total substitution in the 2-O-position could not be estimated in this manner. The ratio of substituents in the 2-O-, 3-O-, and 6-O-positions was found to be 0.64:0.14:1.00 when the amino groups were converted to hydroxyl groups by diazotization, and the distribution was estimated in terms of the 2-hydroxyethyl substituents. It has been observed that a substantial fraction (57.5%) of the 2-O-(2-hydroxyethyl)-D-glucose from the chemically modified cellulose exists in the form of the inner glucosides. Several new monosubstituted glucoses have been prepared and characterized by g.l.c. for this purpose.

The syntheses of simple substituted glucoses (i.e., 2-O-, 3-O-, and 6-O-[(N-methyl-N-2-hydroxyethylamino)ethyl]-D-glucopyranoses) and simple crosslinked glucoses (i.e., N-methylaminobis[O-(N-2-ethyl)-D-glucopyranoses]) with glucose linkages at 2,2′-O-, 3,3′-O-, 6,6′-O-, 2,6′-O-, and 3,6′-O-positions are described. These result from the reactions of "blocked" glucoses with N-methylbis(2-chloroethyl)amine. The new derivatives were characterized by gas–liquid chromatography and electrophoresis. Cotton cellulose modified with N-methylbis(2-chloroethyl)amine to incorporate 0.034 mole of reagent per D-glucopyranosyl unit was hydrolyzed to glucose and substituted glucoses; the substituted glucoses were identified by chromatographic and electrophoretic comparisons with the foregoing authentic glucose derivatives. The relative distribution of (N-methyl-Nhydroxyethylamino)ethyl groups among the 2-O-, 3-O-, and 6-O-positions was 2.30:0.28:1.00. The distribution of crosslinkages among the 2,2′-O-, 2,6′-O-, and 6,6′-O-positions was 2.10:3.72:1.00; these are the only crosslinked derivatives found. The monofunctionally substituted fraction (having a single reagent unit in the substituent group) accounted for 42.6% of the nitrogen; the crosslinked fraction (having a single reagent unit in the crosslink) accounted for 25.8%; complex products accounted for the remainder of the nitrogen of the crosslinked cotton.

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.