150607-94-6

Basic information

• Product Name: Methyl 1,2,3,4-Tetra-O-isobutyryl-b-D-glucopyranuronate
• Synonyms: 3,4,5,6-Tetrakis-isobutyryloxy-tetrahydro-pyran-2-carboxylic Acid Methyl Ester;Methyl 1,2,3,4-Tetra-O-isobutyryl-b-D-glucopyranuronate;Methyl 1,2,3,4-Tetra-O-isobutyryl--D-glucopyranuronate
• CAS NO: 150607-94-6
• Molecular Formula: C₂₃H₃₆O₁₁
• Molecular Weight: 489
• Product Categories: Carbohydrates & Derivatives
• Mol File: 150607-94-6.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 499.3±45.0 °C(Predicted)
• Appearance: /
• Density: 1.18±0.1 g/cm3(Predicted)
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform, Ethyl Acetate
• CAS DataBase Reference: Methyl 1,2,3,4-Tetra-O-isobutyryl-b-D-glucopyranuronate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 1,2,3,4-Tetra-O-isobutyryl-b-D-glucopyranuronate(150607-94-6)
• EPA Substance Registry System: Methyl 1,2,3,4-Tetra-O-isobutyryl-b-D-glucopyranuronate(150607-94-6)

Safety Data

• Hazardous Substances Data: 150607-94-6(Hazardous Substances Data)

Usage

Chemical Properties

Pink Solid

Uses

Methyl 1,2,3,4-Tetra-O-isobutyryl-β-D-glucopyranuronate (cas# 150607-94-6) is a compound useful in organic synthesis.

Upstream product

• 67-56-1 methanol 
• 63-29-6 D-glucurono-6,3-lactone 
• 79-30-1 isobutyryl chloride 
• 533934-74-6 (2S,3S,4S,5R,6R)-1-methyl-3,4,5,6-tetra-hydroxy-tetrahydro-2H-pyran-methylester 
• 1190935-89-7 D-glucurono-6,3-lactone 
• 487-44-5 D-(+)-glucuronic acid γ-lactone 
• 82228-14-6 methyl D-glucopyranuronate 

Downstream Products

• 302965-08-8 C₄₃H₅₃NO₁₃ 
• 70001-26-2 Dihydromorphine 6-β-D-glucuronide 
• 302965-10-2 Methyl (phenyl 2,3,4-tri-O-isobutyryl-1-thio-β-D-glucopyranosid)uronate 
• 934480-58-7 (4S,5R)-bis-isobutyryloxy-(6S)-(2-phenylethyloxy)-tetrahydropyran-(2S)-carboxylic acid methyl ester 

Relevant articles and documents

A convenient new synthesis of quaternary ammonium glucuronides of drug molecules

N-Glucuronides, of various structural types, are frequently encountered as drug metabolites. Efficient chemical synthesis of these compounds, both as analytical standards and for toxicological investigation, is therefore an important goal. Earlier syntheses of N+- glucuronides of aliphatic tertiary amine drugs involved direct reaction of the drug molecule with a bromosugar, but yields were generally low and of poor reproducibility, with many by-products. In addition the final products were often of low stability, hindering effective isolation and purification. We now report that a stable, readily prepared glucuronic acid hemiacetal is a reliable precursor for metabolites of this type and give three pharmaceutically relevant examples. We report further on the stability of the final metabolites and the conditions required for their isolation and purification.

Convenient syntheses of deoxypyranose sugars from glucuronolactone

One of the characteristic reactions of glucuronic acid derivatives is the base-catalysed elimination of a 4-(substituted) hydroxy group to generate a Δ4,5 pyranose. Following hydrogenation, proceeding mainly from the α-face provided the anomeri

Synthesis of a Morphine-6-Glucuronide Hapten, N-(4-Aminobutyl)normorphine-6-Glucuronide, and Related Haptens

For use as a hapten in the radioimmunoassay of morphine-6-glucuronide (2) (M6G), N-(4-aminobutyl)normorphine-6-glucuronide 12 has been prepared, together with related haptens, using the imidate coupling method developed for synthesis of M6G; a rebuttal of recent critical comments on our synthesis of M6G is included.