Glucopyranosiduronic methyl

A number of /i-D-glucopyranosiduronic acids have been prepared from methyl 2,3,4-tri-O-acetyl-1 -bromo-1 -deoxy-/J-D-glucopyranuronate (85), a compound initially prepared by Goebel and Babers by the action of hydrogen bromide in acetic acid on methyl tetra-O-acetyl-a- or fi-D-glucopyranuronates.245... 

To a stirred solution of the methyl 2,3-di-0-benzyl-4-deoxy-a-D-glucopyranosiduronic acid (1.73 g, 4.65 mmol) in CH2CI2 (30 ml) was added oxalyl chloride (0.943 g, 0.65 ml, 7.43 mmol) followed by DMF (0.23 mmol) at room temperature. The resulting clear solution was stirred at room temperature for 2 h, and then concentrated in vacuo. 

In a similar manner, methyl a-D-glucopyranoside (8, R = Me) can be oxidized catalytically in 87% yield to methyl a-D-glucopyranosiduronic acid (9, R = Me). This, however, is only converted to D-glucuronic acid in low yield, because of the necessarily severe conditions of acid hydrolysis. The total yield of n-glucurono-6,3-lactone amounts to 16%. A yield of 68% is obtained from the oxidation of methyl d-D-glucopyranoside. After hydrolysis with formic acid, D-glucurono-6,3-lactone is obtained in an over-all yield of 15%. 

Synonyms a-d-Glucopyranosiduronic acid, (3p,20p)-20-carboxy-11 -oxo-30-norolean-12-en-3-yl 2-o-P-d-glucopyranuronosyl-, methyl ester... 

Li K, Helm R (1995) A practical synthesis of methyl 4-O-methyl-a-D-glucopyranosiduronic acid. Carbohydr Res 273 249... 

Me glycoside Methyl 4-amino-4-deoxy-a-D-glucopyranosiduronic acid, SCI [26302-28-3]... 

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