42868-84-8

Upstream product

• 485-72-3 7-Hydroxy-3-(4-methoxy-phenyl)-chromen-4-on 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 108-24-7 acetic anhydride 
• 487-49-0 1-(2,4-dihydroxyphenyl)-2-(4-methoxyphenyl)ethanone 
• 104-47-2 p-methoxybenzylnitrile 
• 108-46-3 recorcinol 
• 604-69-3 β-D-glucose pentaacetate 
• 6919-96-6 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 42868-73-5 2-hydroxy-4-(β-D-tetra-O-acetylglucopyranosyloxy)phenyl 4-methoxybenzyl ketone 
• 122-51-0 orthoformic acid triethyl ester 

Downstream Products

• 486-62-4 ononin 

Relevant academic research and scientific papers

The phase transfer catalysed synthesis of isoflavone-O-glucosides

Daidzin 1, genistin 2, ononin 3 and sissotrin 4 are the major products of the phase transfer catalysed reaction between the isoflavone aglycones daidzein, genistein, formononetin and biochanin A, respectively, and 1-bromo-2,3,4,6-tetra-O-acetyl-α-glucopyranose. Complete proton and carbon NMR assignments are presented for compounds 1-4.

TEMPO-Mediated Regiospecific Oxidation of Glucosides to Glucuronides

A TEMPO/hypochlorite/bromide oxidant has been used for the conversion of aryl and steroidal glucosides to the corresponding glucuronide conjugates in good (48-74%) yield. An isoflavone glucoside failed to undergo this transformation.

EFFECTIVE SYNTHESIS OF 7-HYDROXYISOFLAVONE O-GLUCOSIDES

An effective procedure for condensing acetobromoglucose with 2,4-dihydroxy phenyl benzyl ketones has been developed.The 2-hydroxy-4-(β-D-tetra-O-acetylglucopyranosyloxy)phenyl benzyl ketones synthesized with yields of 47-69percent have been converted under the action of ethyl orthoformate in pyridine solution into 7-hydroxyisoflavone O-glukosides and these have also been obtained by the glycosylation of 7-hydroxyisoflavone.The advantages and disadvantages of the alternative pathways of the synthesis of 7-hydroxyisoflavone O-glykosides are discussed.