158419-85-3

Basic information

• Product Name: (Methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-4-retinamidophenylmethane
• CAS NO: 158419-85-3
• Molecular Weight: 705.846
• Mol File: 158419-85-3.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (Methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-4-retinamidophenylmethane(CAS DataBase Reference)
• NIST Chemistry Reference: (Methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-4-retinamidophenylmethane(158419-85-3)
• EPA Substance Registry System: (Methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-4-retinamidophenylmethane(158419-85-3)

Safety Data

• Hazardous Substances Data: 158419-85-3(Hazardous Substances Data)

Upstream product

• 155590-31-1 (2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl)phenylmethane 
• 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 
• 136034-23-6 β-D-Glucopyranosylphenylmethane 
• 100-44-7 benzyl chloride 
• 302-79-4 all-trans-retinoic-acid 
• 67773-43-7 2,3,4,6-tetra-O-benzyl-α/β-D-glucopyranosyl bromide 
• 158419-83-1 (methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-4-nitzrophenylmethane 
• 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 
• 158419-84-2 (Methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-4-aminophenylmethane 

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.