698358-03-1

Basic information

• Product Name: ALLYL D-GLUCURONATE
• Synonyms: ALLYL D-GLUCURONATE;alpha-D-Glucopyranuronic acid 2-propenyl ester
• CAS NO: 698358-03-1
• Molecular Formula: C9H14O7
• Molecular Weight: 234.20326
• Product Categories: 13C & 2H Sugars;Carbohydrates & Derivatives
• Mol File: 698358-03-1.mol
• Article Data: 11

Chemical Properties

• Appearance: /
• Storage Temp.: Amber Vial, -86°C Freezer, Under inert atmosphere
• Solubility: Acetonitrile (Slightly), Methanol (Slightly), Water (Slightly)
• Stability: Light Sensitive, Temperature Sensitive
• CAS DataBase Reference: ALLYL D-GLUCURONATE(CAS DataBase Reference)
• NIST Chemistry Reference: ALLYL D-GLUCURONATE(698358-03-1)
• EPA Substance Registry System: ALLYL D-GLUCURONATE(698358-03-1)

Safety Data

• Hazardous Substances Data: 698358-03-1(Hazardous Substances Data)

Usage

Chemical Properties

Off-White Solid

Uses

It is used in efficient synthesis of 1β-O-acyl glucuronides via regioselective acylation of allyl or benzyl D-glucuronate.Αcyl glucuronides are known metabolites of important drugs.

Upstream product

• 6556-12-3 D-glucuronic acid 
• 106-95-6 allyl bromide 
• 104195-06-4 L-glucuronic acid 
• 912483-14-8 galacturonic acid 
• 489-91-8 D-glucuronic acid 
• 6556-12-3 D-Glucuronic acid 

Downstream Products

• 1184951-57-2 allyl 6-([4-([1-(tert-butyl)-1,1-dimethylsilyl]oxymethyl)anilino]carbonyloxy)-3,4,5-trihydroxytetrahydro-2H-2-pyrancarboxylate 

Relevant articles and documents

Plasma stability-dependent circulation of acyl glucuronide metabolites in humans: How circulating metabolite profiles of muraglitazar and peliglitazar can lead to misleading risk assessment

Muraglitazar and peliglitazar, two structural analogs differing by a methyl group, are dual peroxisome proliferator-activated receptor- α/γ activators. Both compounds were extensively metabolized in humans through acyl glucuronidation to form 1-O-β-acyl g

The practical synthesis of β-acyl glucuronides by using allyl 2,3,4-tri-(O-allyloxycarbonyl)-D-glucuronate and 1-chloro-N,N,2-trimethyl-1-propenylamine

We described the practical synthesis of β-acyl glucuronide from allyl 2,3,4-tri-(O-allyloxycarbonyl)-D-glucuronate (5) mediated by 1-chloro-N,N,2-trimethyl-1-propenylamine (TMCE). A wide range of bulky carboxylic acids (aryl carboxylic acids or tertiary-carbon-linked carboxylic acids) were employed to give the corresponding β-acyl glucuronate in good yields. The side products of this reaction are only N,N-dimethylisobutyramide and HCl. As the resulting acyl glucuronates show sufficient solubility to organic solvent, it can be easily purified by conventional silica gel column chromatography and/or crystallization, even in multigram quantities. The allyloxycarbonyl group and allyl group are cleanly removed by Pd(0), and thus the protocol can provide multigram quantities of β-acyl glucuronides with high purity.

Synthesis of three isotopically labeled versions and a metabolite of Aurora A kinase inhibitor

Sodium ring-[14C]-4-[[9-chloro-7-(2,6-difluorophenyl)-5H- pyrimido[5,4-d][2]benzazepin-2-yl]amino]-benzoate (1A, MLN8054), an Aurora A kinase inhibitor, was synthesized from [14C]-cyanamide in two steps in an overall radiochemical yi