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

Description

ALLYL D-GLUCURONATE is a chemical compound derived from D-glucuronate, which is a natural sugar found in the body. It is known for its ability to undergo regioselective acylation, making it a valuable intermediate in the synthesis of 1β-O-acyl glucuronides.

Uses

Used in Pharmaceutical Industry:
ALLYL D-GLUCURONATE is used as an intermediate in the efficient synthesis of 1β-O-acyl glucuronides, which are known metabolites of important drugs. This application is crucial for the development of new drugs and the improvement of existing ones, as it allows for the creation of more effective and targeted therapies.
Used in Drug Metabolism Research:
ALLYL D-GLUCURONATE is used as a research tool for studying the metabolism of drugs and their glucuronidation pathways. Understanding these pathways is essential for predicting drug interactions, side effects, and overall safety, as well as for optimizing drug dosing and efficacy.

Upstream product

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

Downstream Products

• 99043-04-6 Mycophenolic acid acyl glucuronide 

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