113114-66-2

Upstream product

• 108-24-7 acetic anhydride 
• 13231-13-5 (2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)benzene 
• 108-86-1 bromobenzene 
• 5627-22-5 (2R,3S,4R,5R,6S)-2-(hydroxymethyl)-6-phenyltetrahydro-2H-pyran-3,4,5-triol 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 

Downstream Products

• 28836-04-6 1-(β-D-glucopyranosyl)-4-nitrobenzene 
• 113092-87-8 4-(2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl)aniline 
• 101116-21-6 (1S)-1-(4-acetylamino-phenyl)-1,5-anhydro-D-glucitol 
• 102477-17-8 (1S)-tetra-O-acetyl-1-(4-acetylamino-phenyl)-1,5-anhydro-D-glucitol 

Relevant academic research and scientific papers

PREPARATION OF 4-RETINAMIDOPHENYL- AND 4-RETINAMIDOBENZYL-C-GLYCOSYL AND C-GLUCURONOSYL ANALOGUES OF THE GLUCURONIDE OF 4-HYDROXYPHENYLRETINAMIDE AS POTENTIAL STABLE CANCER CHEMOPREVENTIVE AGENTS

Glucuronide metabolites of retinoic acid and its analogues have been suggested to be active cancer chemopreventive analogues of the parent molecules.However, these metabolites are susceptible to β-glucuronidase and acid-catalyzed cleavage and it is not clear whether these carbohydrate conjugates must be hydrolyzed back to the parent molecule to show activity.Thus, the multistep syntheses of stable C-glycosyl and C-glucuronosyl analogues of the known glucuronide metabolite of the breast cancer chemopreventive agent 4-hydroxyphenylretinamide (4-HPR) are outlined.The chemical and enzymatic stability of these compounds has been evaluated relative to the glucuronide of 4-HPR.