Synthesis of 4-O-(beta-D-Glucopyranosiduronic Acid)-dopamine.

Abstract
4-O-(.beta.-D-Glucopyranosiduronic acid)-dopamine was synthesized for comparison with a substance with identical properties present in a golden hamster islet cell tumor. The compound was prepared by ion pair alkylation of tetrabutylammonium 2-benzyloxy-4-formylphenolate with methyl (2,3,4-tri-O-acetyl-.alpha.-D-glucopyranosyl bromide) uronate followed by nitromethylation of the aldehyde function, catalytic hydrogenation of the nitrostyrene derivative to a saturated amine with simultaneous removal of the benzylic group and final hydrolysis of the ester functions. Ion pair alkylation afforded a convenient route to this glycoside.
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