Pioglitazone Thiazolidinedione Ring-opened N-β-D-Glucuronide

Base Information

• Chemical Name: Pioglitazone Thiazolidinedione Ring-opened N-β-D-Glucuronide
• CAS No.: 1296832-76-2
• Molecular Formula: C25H30N2O10S
• Molecular Weight: 550.5781
• Mol file: 1296832-76-2.mol

Synonyms:Pioglitazone Thiazolidinedione Ring-opened N-β-D-Glucuronide;1-[[[[1-Carboxy-2-[4-[2-(5-ethyl-2-pyridinyl)ethoxy]phenyl]ethyl]thio]carbonyl]aMino]-1-deoxy-β-D-glucopyranuronic Acid

Chemical Property of Pioglitazone Thiazolidinedione Ring-opened N-β-D-Glucuronide

Chemical Property:

• PKA: 2.81±0.70(Predicted)
• PSA: 224.53000
• Density: 1.50±0.1 g/cm3(Predicted)
• LogP: 0.80060

Purity/Quality:

98%min ^*data from raw suppliers

PioglitazoneThiazolidinedioneRing-openedN-β-D-Glucuronide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Pioglitazone Thiazolidinedione Ring-opened N-β-D-Glucuronide

There total 6 articles about Pioglitazone Thiazolidinedione Ring-opened 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-carboxy-3,4,5-trihydroxy-tetrahydropyran-2-yl)-5-{4-[2-(5-ethyl-2-pyridinyl)ethoxy]benzyl}-thiazolidine-2,4-dione trifluoroacetate → (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 (1296832-76-2)

Guidance literature:

With sodium acetate; In water; acetonitrile; at 20 ℃; for 296h;

DOI:10.1124/dmd.109.031583

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) → (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 (1296832-76-2)

Guidance literature:

Multi-step reaction with 3 steps

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

2: water; acetonitrile

3: sodium acetate / water; acetonitrile / 296 h / 20 °C

With morpholine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium acetate; In dichloromethane; water; acetonitrile;

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) → (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 (1296832-76-2)

Guidance literature:

Multi-step reaction with 5 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

4: water; acetonitrile

5: sodium acetate / water; acetonitrile / 296 h / 20 °C

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

DOI:10.1124/dmd.109.031583

upstream raw materials:

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

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