Studies of D-Glucuronolactone Derivatives. V

Abstract

Methyl (2-chloroethyl-2, 3, 4-tri-O-acetyl-β-D-glucopyranosid) uronate (II) was prepared by the reaction of methyl 1-bromo-1-deoxy-tri-O-acetyl-α-glucopyranuronate and 2-chloroethanol, in the presence of silver carbonate, Treatment of II with methanolic ammonia afforded 2-chloroethyl β-D-glucopyranosiduronamide (III) which agreed with the product obtained from 1-bromo-1-deoxy-tri-O-acetyl-α-glucopyranuronamide (V). Treatment of II with trimethylamine solution gave 2-aminoethyl β-D-glucopyranosiduronic acid trimethyl betaine (XV). 2-Alkylaminoethyl β-D-glucopyranosiduronamides (VI to X) were obtained by the application of various amines to III.It was found that application of dimethylamine solution to II produced 2-dimethylaminoethyl β-D-glucopyranosiduronic acid (XVI), N, N-dimethyl (2-chloroethyl-β-D-glucopyranosid) uronamide (XVIII), and N, N-dimethyl (2-dimethylaminoethyl-β-D-glucopyranosid) uronamide (XIX), and their structure was established.