Glucuronic acid methyl ester

The HMBC spectrum also displayed the interaction between GluAMe.H-1 with the aglycone C-3, connecting this glucuronic acid methyl ester moiety to the aglycone 3-position. 

S). Upon acetylation and esterification, the natural product gives a tri-0-acetyl methyl ester. This product is identical with that obtained by the reaction of 1-bromotetra-O-acetyl-D-glucuronic acid methyl ester with silver benzoate and must have the 0-benzoyl group at carbon 1. 

W. F. Goebel and F. H. Babers, Derivatives of glucuronic acid. VI. The preparation of a-chloro- and of-bromotriacctylglucuronic acid methyl ester, and the synthesis of /fglucuronidcs,. /. Biol. Chem., Ill (1933) 347-353. 

A series of derivatives analogous to those from D-glucuronic acid has been made by Morell and Link.68 An important compound is the crystalline methyl ester of methyl a-D-galacturonoside (XXXII) which on alkaline hydrolysis yields methyl a-D-galacturonoside (XXXIII). Since... 

Figure 3.8(a) Possible ester linkage between an a-OH of lignin and a carboxyl group of a 4-0-methyl-/3-d-glucuronic acid residue on the xylan backbone. 

The glucuronic acid moiety of bomyl /9-D-glucuronide excreted as a metabolite of bomeol by man or rabbit was shown by Pryde and Williams20 to have a pyranoid structure. The glucuronide, on treatment with methyl iodide and silver oxide, gave crystalline bomyl 2,3,4-tri-O-methyl-jS-D-glucuronide methyl ester. This was converted to a mixture of a and (8 anomers of methyl tri-O-methyl-D-glucuronides by the action of 0.2 N sulfuric acid in methanol at 100° under pressure. Oxidation of... 

A. F. Bochkov and Ya. V. Voznyi, Sugar ortho esters. Part 8. Synthesis of 4-O-methyl-D-glucuronic acid derivatives, Carbohydr. Res., 32 (1974) 1-8. 

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