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

Base Information

• Chemical Name: 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
• CAS No.: 1296832-69-3
• Molecular Formula: C₃₂H₃₆N₂O₁₂S
• Molecular Weight: 672.71
• Mol file: 1296832-69-3.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 1 articles about 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 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: 83.0%

5-{4-[2-(5-ethyl-2-pyridyl)ethoxy]benzyl}-2,4-thiazolidinedione hydrochloride (112529-15-4) + 1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester (21085-72-3) → 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 (1296832-69-3)

Guidance literature:

With caesium carbonate; In acetonitrile; at 70 ℃; for 3h;

DOI:10.1124/dmd.109.031583

Reference yield: 85.0%

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 (1296832-69-3) + allyl alcohol (107-18-6) → 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)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; at 20 ℃; for 76h;

DOI:10.1124/dmd.109.031583

Reference yield:

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 (1296832-69-3) → 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 trifluoroacetate

Guidance literature:

Multi-step reaction with 3 steps

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

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

3: water; acetonitrile

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

DOI:10.1124/dmd.109.031583

upstream raw materials:

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:

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

(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

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