158419-84-2

Basic information

• Product Name: (Methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-4-aminophenylmethane
• Synonyms: (Methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-4-aminophenylmethane
• CAS NO: 158419-84-2
• Molecular Weight: 423.42
• Mol File: 158419-84-2.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (Methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-4-aminophenylmethane(CAS DataBase Reference)
• NIST Chemistry Reference: (Methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-4-aminophenylmethane(158419-84-2)
• EPA Substance Registry System: (Methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-4-aminophenylmethane(158419-84-2)

Safety Data

• Hazardous Substances Data: 158419-84-2(Hazardous Substances Data)

Upstream product

• 158419-81-9 (Methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)phenylmethane 
• 54423-54-0 2,3,4,6-Tetra-O-benzyl 1-O-p-nitrobenzoyl D-glucopyranoside 
• 136034-24-7 (2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)phenylmethane 
• 100-44-7 benzyl chloride 
• 67773-43-7 2,3,4,6-tetra-O-benzyl-α/β-D-glucopyranosyl bromide 
• 155590-31-1 (2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl)phenylmethane 
• 478068-25-6 (2R,3R,4R,5S,6S)-3,4,5-Tris-methoxymethoxy-2-methoxymethoxymethyl-6-(4-nitro-benzyl)-tetrahydro-pyran 
• 90-80-2 D-Glucono-1,5-lactone 
• 189825-51-2 2,3,4,6-tetra-O-(methoxymethyl)-δ-D-gluconolactone 
• 189825-52-3 (2R,3R,4S,5R)-3,4,5-tris(methoxymethoxy)-2-((methoxymethoxy)methyl)-6-methylenetetrahydro-2H-pyran 
• 158419-83-1 (methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-4-nitzrophenylmethane 

Downstream Products

• 158419-85-3 (Methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-4-retinamidophenylmethane 

Relevant articles and documents

An improved synthesis of the C-linked glucuronide of N-(4-hydroxyphenyl)retinamide.

Retinoic acid analogues such as N-(4-hydroxyphenyl)retinamide (4-HPR) are effective chemopreventatives and chemotherapeutics for numerous types of cancer. The C-linked analogue of the O-glucuronide of 4-HPR (4-HPRCG) has been shown to be a more effective agent. The synthetic route to this molecule has been significantly improved by access to a key C-benzyl-glucuronide intermediate through employment of a Suzuki coupling reaction between an exoanomeric methylene sugar and an aryl bromide. Preliminary evidence shows 4-HPRCG has chemotherapeutic activity.

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.