Pioglitazone N-β-D-Glucuronide

Base Information

• Chemical Name: Pioglitazone N-β-D-Glucuronide
• CAS No.: 1296832-75-1
• Molecular Formula: C25H28N2O9S
• Molecular Weight: 532.56282
• Mol file: 1296832-75-1.mol

Synonyms:Pioglitazone N-β-D-Glucuronide;1-Deoxy-1-[5-[[4-[2-(5-ethyl-2-pyridinyl)ethoxy]phenyl]Methyl]-2,4-dioxo-3-thiazolidinyl] β-D-Glucopyranuronic Acid;Pioglitazone N-beta-D-Glucuronide (Mixture of Diastereomers)

Chemical Property of Pioglitazone N-β-D-Glucuronide

Chemical Property:

• Boiling Point: 790.9±70.0 °C(Predicted)
• PKA: 2.85±0.70(Predicted)
• PSA: 192.02000
• Density: 1.512±0.06 g/cm3(Predicted)
• LogP: 0.70210

Purity/Quality:

95%+ or 98%+ ^*data from raw suppliers

Pioglitazone N-β-D-Glucuronide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: A metabolite of Pioglitazone (P471015) formed via N-glucuronidation of thiazolidinedione ring.

Technology Process of Pioglitazone N-β-D-Glucuronide

There total 4 articles about Pioglitazone N-β-D-Glucuronide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

3-((2R,3R,4S,5S,6S)-6-allyloxycarbonyl-3,4,5-trihydroxy-tetrahydropyran-2-yl)-5-{4-[2-(5-ethyl-2-pyridinyl)ethoxy]benzyl}-thiazolidine-2,4-dione (1296832-72-8) → 3-((2R,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxy-tetrahydropyran-2-yl)-5-{4-[2-(5-ethyl-2-pyridinyl)ethoxy]benzyl}-thiazolidine-2,4-dione (1296832-75-1)

Guidance literature:

With morpholine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In dichloromethane; at 20 ℃; for 4h;

DOI:10.1124/dmd.109.031583

Reference yield:

1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester (21085-72-3) → 3-((2R,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxy-tetrahydropyran-2-yl)-5-{4-[2-(5-ethyl-2-pyridinyl)ethoxy]benzyl}-thiazolidine-2,4-dione (1296832-75-1)

Guidance literature:

Multi-step reaction with 3 steps

1: caesium carbonate / acetonitrile / 3 h / 70 °C

2: hydrogenchloride / 1,4-dioxane / 76 h / 20 °C

3: morpholine; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / dichloromethane / 4 h / 20 °C

With morpholine; hydrogenchloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; caesium carbonate; In 1,4-dioxane; dichloromethane; acetonitrile;

DOI:10.1124/dmd.109.031583

Reference yield:

5-{4-[2-(5-ethyl-2-pyridyl)ethoxy]benzyl}-2,4-thiazolidinedione hydrochloride (112529-15-4) → 3-((2R,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxy-tetrahydropyran-2-yl)-5-{4-[2-(5-ethyl-2-pyridinyl)ethoxy]benzyl}-thiazolidine-2,4-dione (1296832-75-1)

Guidance literature:

Multi-step reaction with 3 steps

1: caesium carbonate / acetonitrile / 3 h / 70 °C

2: hydrogenchloride / 1,4-dioxane / 76 h / 20 °C

3: morpholine; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / dichloromethane / 4 h / 20 °C

With morpholine; hydrogenchloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; caesium carbonate; In 1,4-dioxane; dichloromethane; acetonitrile;

DOI:10.1124/dmd.109.031583

upstream raw materials:

3-((2R,3R,4S,5S,6S)-3,4,5-triacetoxy-6-methoxycarbonyl-tetrahydropyran-2-yl)-5-{4-[2-(5-ethyl-2-pyridinyl)ethoxy]benzyl}-thiazolidine-2,4-dione

3-((2R,3R,4S,5S,6S)-6-allyloxycarbonyl-3,4,5-trihydroxy-tetrahydropyran-2-yl)-5-{4-[2-(5-ethyl-2-pyridinyl)ethoxy]benzyl}-thiazolidine-2,4-dione

5-{4-[2-(5-ethyl-2-pyridyl)ethoxy]benzyl}-2,4-thiazolidinedione hydrochloride

1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester

Downstream raw materials:

(2S,3S,4S,5R,6R)-6-(1-carboxy-2-{4-[2-(5-ethyl-2-pyridinyl)ethoxy]phenyl}-ethylsulfanylcarbonylamino)-3,4,5-trihydroxy-tetrahydropyran-2-carboxylic acid