5,5'-bis-(4-[2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy]phenyl)-[2,2']-bithiophene

Base Information

• Chemical Name: 5,5'-bis-(4-[2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy]phenyl)-[2,2']-bithiophene
• CAS No.: 1262996-39-3
• Molecular Formula: C₄₈H₅₀O₂₀S₂
• Molecular Weight: 1011.05
• Mol file: 1262996-39-3.mol

Synonyms:5,5'-bis-(4-[2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy]phenyl)-[2,2']-bithiophene

Chemical Property of 5,5'-bis-(4-[2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy]phenyl)-[2,2']-bithiophene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5,5'-bis-(4-[2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy]phenyl)-[2,2']-bithiophene

There total 4 articles about 5,5'-bis-(4-[2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy]phenyl)-[2,2']-bithiophene 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: 91.0%

(2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(4-iodophenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate (669763-44-4) + 5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene (239075-02-6) → 5,5'-bis-(4-[2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy]phenyl)-[2,2']-bithiophene (1262996-39-3)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; silver(l) oxide; In 1,4-dioxane; at 70 ℃; Inert atmosphere;

DOI:10.1016/j.tet.2010.11.004

Reference yield:

D-glucose pentaacetate (83-87-4,604-68-2,604-69-3,2152-77-4,4026-35-1,4163-59-1,4163-60-4,4163-61-5,4163-65-9,4257-94-7,4257-96-9,16299-15-3,19186-39-1,19189-55-0,25878-60-8,25941-03-1,32445-48-0,32445-49-1,32445-53-7,32445-54-8,34685-58-0,34685-59-1,43168-42-9,43168-44-1,43169-22-8,43169-25-1,66966-07-2,70749-17-6,80184-01-6,93221-01-3,93221-02-4,99630-88-3,109215-53-4,115792-70-6,115792-73-9,139894-92-1,139973-25-4,144071-49-8,147648-81-5) → 5,5'-bis-(4-[2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy]phenyl)-[2,2']-bithiophene (1262996-39-3)

Guidance literature:

Multi-step reaction with 2 steps

1: boron trifluoride diethyl etherate / dichloromethane / 12 h / 20 °C / Inert atmosphere

2: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; silver(l) oxide / 1,4-dioxane / 70 °C / Inert atmosphere

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; boron trifluoride diethyl etherate; sodium carbonate; silver(l) oxide; In 1,4-dioxane; dichloromethane; 2: Suzuki-Miyaura coupling;

DOI:10.1016/j.tet.2010.11.004

Reference yield:

p-Iodophenol (540-38-5) → 5,5'-bis-(4-[2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy]phenyl)-[2,2']-bithiophene (1262996-39-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 1,1,1,3,3,3-hexamethyl-disilazane / acetonitrile / 12 h / 20 °C / Inert atmosphere

2: boron trifluoride diethyl etherate / dichloromethane / 12 h / 20 °C / Inert atmosphere

3: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; silver(l) oxide / 1,4-dioxane / 70 °C / Inert atmosphere

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; boron trifluoride diethyl etherate; sodium carbonate; 1,1,1,3,3,3-hexamethyl-disilazane; silver(l) oxide; In 1,4-dioxane; dichloromethane; acetonitrile; 3: Suzuki-Miyaura coupling;

DOI:10.1016/j.tet.2010.11.004

upstream raw materials:

(2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(4-iodophenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate

5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene

D-glucose pentaacetate

p-Iodophenol