Benzyl 2,3,4-tri-O-benzyl-β-d-glucopyranosiduronic acid and some related compounds

Add time:08/25/2019    Source:sciencedirect.com

A d-glucuronic acid derivative fully protected with hydrogenolyzable groups except at C-6 has been synthesized. Successive tritylation and benzoylation of benzyl β-d-glucopyranoside gave benzyl 2,3,4-tri-O-benzoyl-6-O-trityl-β-d-glucopyranoside (1). The benzoyl groups in 1 were replaced with benzyl groups to give 2, and the trityl group was then removed by hydrolysis, giving benzyl 2,3,4-tri-O-benzyl-β-d-glucopyranoside (3). Oxidation of 3 with the Pfitzner-Moffatt reagent afforded the corresponding aldehyde (4), which was further oxidized, with iodine and methanolic potassium hydroxide, to the methyl ester 6. Alkaline hydrolysis of 6 gave the desired d-glucuronic acid derivative, benzyl 2,3,4-tri-O-benzyl-β-d-glucopyranosiduronic acid (5). The conversion of 3 into 5 was also achieved, in a one-step process, through the use of chromium trioxide and dilute sulfuric acid in acetone. The ester, 6, was further characterized through the corresponding amide (8), and the steric accessibility of the carboxyl group in 5 was demonstrated through its conversion into the 2-naphthyl ester (7).

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