55331-64-1

Upstream product

• 186581-53-3 diazomethane 
• 929879-91-4 cyclohexyl 2,3,4-tri-O-acetyl-β-D-glucopyranosiduronic acid 
• 108-93-0 cyclohexanol 
• 21085-72-3 1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester 
• 92420-89-8 methyl 2,3,4-tri-O-acetyl-1-O-(trichloroacetimidoyl)-α-D-glucopyranuronate 
• 6919-98-8 2,3,4-tri-O-acetyl-1-bromo-1-deoxy-β-D-glucopyranuronic acid methy ester 

Downstream Products

• 439905-48-3 O¹-cyclohexyl-β-D-glucopyranuronic acid methyl ester 
• 5285-00-7 O¹-cyclohexyl-β-D-glucopyranuronic acid 

Relevant academic research and scientific papers

Glycosidation-anomerisation reactions of 6,1-anhydroglucopyranuronic acid and anomerisation of β-D-glucopyranosiduronic acids promoted by SnCl 4

The reaction of silylated nucleophiles with 6,1-anhydroglucopyranuronic acid (glucuronic acid 6,1-lactones) catalysed by tin(IV) chloride provides 1,2-trans or 1,2-cis (deoxy)glycosides in a manner dependent on the donor structure. The α-glycoside was obt

Putative metabolites of fulvestrant, an estrogen receptor downregulator. Improved glucuronidation using trichloroacetimidates

Following regioselective protection of the estrogen receptor downregulator fulvestrant (ICI 182,780) 1 as its 17-acetate 2 or 3-benzoate 4, the 3-sulfate 5 and 3- and 17-glucuronide conjugates 8 and 12 were prepared. Satisfactory preparation of 12 required use of the tri-O-isobutyryl imidate derivative 10 in conjunction with an inverse-addition technique not previously employed in glucuronidation. The value of this method for simpler aglycones is discussed together with a study of variations in donor acyl substituent and catalyst. Another putative metabolite, the 17-ketone 19, was prepared by direct oxidation of 1.

Glucuronide and sulfate conjugates of ICI 182,780, a pure anti- estrogenic steroid. Order of addition, catalysis and substitution effects in glucuronidation

The 3-sulfate 4 and 3- and 17-glucuronide conjugates 5 and 6 of the pure anti-estrogenic steroid ICI 182,780 1, which is expected to be an effective agent for the treatment of breast cancer, have been prepared. The synthesis of 6 could only be satisfactorily achieved using an inverse addition technique, not previously employed in the glucuronic acid series: the value of this technique for some other aglycones is discussed.

Substrate Specificity of Glycyrrhizinic Acid Hydrolase

Glycyrrhizinic acid hydrolase produced by Aspergillus niger selectively hydrolyzed the 3-O-β-D-glucuronide linkage of glycyrrhizinic acid.The substrate specificity of this enzyme was investigated for synthetic glucuronides of aliphatic alcohols as well as natural glucuronide saponins.It was revealed that the glucuronide linkage with low molecular weight alcohols was not cleaved by this enzyme, while the 3-O-β-D-glucuronide linkage saponins of oleanolic acid was selectively hydrolyzed.It was also disclosed that both the 4-hydroxyl and carboxyl groups of the glucuronide moiety must be unsubstituted for hydrolysis by this enzyme.