(2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-((5-hydroxy-2-(4-methoxyphenyl)-4-oxo-4H-chromen-7-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Base Information

• Chemical Name: (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-((5-hydroxy-2-(4-methoxyphenyl)-4-oxo-4H-chromen-7-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate
• CAS No.: 1389307-17-8
• Molecular Formula: C₃₀H₃₀O₁₄
• Molecular Weight: 614.56
• Mol file: 1389307-17-8.mol

Synonyms:(2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-((5-hydroxy-2-(4-methoxyphenyl)-4-oxo-4H-chromen-7-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Chemical Property of (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-((5-hydroxy-2-(4-methoxyphenyl)-4-oxo-4H-chromen-7-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-((5-hydroxy-2-(4-methoxyphenyl)-4-oxo-4H-chromen-7-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate

There total 4 articles about (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-((5-hydroxy-2-(4-methoxyphenyl)-4-oxo-4H-chromen-7-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate 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: 83.11%

2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide (572-09-8,3068-32-4,4026-32-8,6919-96-6,13242-53-0,14227-54-4,14795-18-7,19186-59-5,19285-38-2,21698-13-5,29907-26-4,53369-42-9,60619-58-1,61303-35-3,67337-79-5,69127-37-3,70749-15-4,72002-90-5,75247-30-2,75880-74-9,78418-57-2,102339-89-9,102339-90-2,103530-40-1,114028-03-4,114718-45-5,138514-70-2,138514-71-3) + 5,7-dihydroxy-2-(4'-methoxyphenyl)-4H-1-benzopyran-4-one (480-44-4) → (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-((5-hydroxy-2-(4-methoxyphenyl)-4-oxo-4H-chromen-7-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate (1389307-17-8)

Guidance literature:

With tetrabutylammomium bromide; potassium carbonate; In chloroform; at 45 ℃; for 12h; regioselective reaction; Inert atmosphere;

DOI:10.1016/j.carres.2012.05.013

Reference yield:

naringin (10236-47-2) → (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-((5-hydroxy-2-(4-methoxyphenyl)-4-oxo-4H-chromen-7-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate (1389307-17-8)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine; iodine / 2 h / 95 °C

2: sodium hydroxide / water / 6.5 h / 10 - 25 °C

3: sulfuric acid; water / 8 h / Reflux

4: tetrabutylammomium bromide; potassium carbonate / chloroform / 12 h / 45 °C / Inert atmosphere

With pyridine; sulfuric acid; tetrabutylammomium bromide; water; iodine; potassium carbonate; sodium hydroxide; In chloroform; water;

DOI:10.1016/j.carres.2012.05.013

Reference yield:

apigenin 7-O-neohesperidoside → (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-((5-hydroxy-2-(4-methoxyphenyl)-4-oxo-4H-chromen-7-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate (1389307-17-8)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium hydroxide / water / 6.5 h / 10 - 25 °C

2: sulfuric acid; water / 8 h / Reflux

3: tetrabutylammomium bromide; potassium carbonate / chloroform / 12 h / 45 °C / Inert atmosphere

With sulfuric acid; tetrabutylammomium bromide; water; potassium carbonate; sodium hydroxide; In chloroform; water;

DOI:10.1016/j.carres.2012.05.013

upstream raw materials:

naringin

2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide

5,7-dihydroxy-2-(4'-methoxyphenyl)-4H-1-benzopyran-4-one

rhoifolin

Downstream raw materials:

tilianin