(2S,3S,4S,5R,6S)-6-{3,5-Dihydroxy-4-[(E)-3-(4-hydroxy-phenyl)-acryloyl]-phenoxy}-3,4,5-trihydroxy-tetrahydro-pyran-2-carboxylic acid

Base Information

• Chemical Name: (2S,3S,4S,5R,6S)-6-{3,5-Dihydroxy-4-[(E)-3-(4-hydroxy-phenyl)-acryloyl]-phenoxy}-3,4,5-trihydroxy-tetrahydro-pyran-2-carboxylic acid
• CAS No.: 929051-24-1
• Molecular Formula: C₂₁H₂₀O₁₁
• Molecular Weight: 448.383
• Mol file: 929051-24-1.mol

Synonyms:

Chemical Property of (2S,3S,4S,5R,6S)-6-{3,5-Dihydroxy-4-[(E)-3-(4-hydroxy-phenyl)-acryloyl]-phenoxy}-3,4,5-trihydroxy-tetrahydro-pyran-2-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4S,5R,6S)-6-{3,5-Dihydroxy-4-[(E)-3-(4-hydroxy-phenyl)-acryloyl]-phenoxy}-3,4,5-trihydroxy-tetrahydro-pyran-2-carboxylic acid

There total 4 articles about (2S,3S,4S,5R,6S)-6-{3,5-Dihydroxy-4-[(E)-3-(4-hydroxy-phenyl)-acryloyl]-phenoxy}-3,4,5-trihydroxy-tetrahydro-pyran-2-carboxylic acid 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:

(2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-[2-(4-acetoxy-phenyl)-5-hydroxy-4-oxo-chroman-7-yloxy]-tetrahydro-pyran-2-carboxylic acid methyl ester → (2S,3S,4S,5R,6S)-6-{3,5-Dihydroxy-4-[(E)-3-(4-hydroxy-phenyl)-acryloyl]-phenoxy}-3,4,5-trihydroxy-tetrahydro-pyran-2-carboxylic acid (929051-24-1)

Guidance literature:

With sodium carbonate; In methanol; for 2.5h;

DOI:10.1002/jms.1050

Reference yield:

4'-O-acetylnaringenin → (2S,3S,4S,5R,6S)-6-{3,5-Dihydroxy-4-[(E)-3-(4-hydroxy-phenyl)-acryloyl]-phenoxy}-3,4,5-trihydroxy-tetrahydro-pyran-2-carboxylic acid (929051-24-1)

Guidance literature:

Multi-step reaction with 2 steps

1: Ag₂O; pyridine; molecular sieves 4 Angstroem / 16 h

2: aq. Na₂CO₃ / methanol / 2.5 h

With pyridine; 4 A molecular sieve; sodium carbonate; silver(l) oxide; In methanol;

DOI:10.1002/jms.1050

Reference yield:

2-(4-acetoxyphenyl)-5-hydroxy-4-oxochroman-7-yl acetate (3162-03-6) → (2S,3S,4S,5R,6S)-6-{3,5-Dihydroxy-4-[(E)-3-(4-hydroxy-phenyl)-acryloyl]-phenoxy}-3,4,5-trihydroxy-tetrahydro-pyran-2-carboxylic acid (929051-24-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 63 percent / aq. imidazolium hydrochloride / tetrahydrofuran / 2.5 h / 20 °C

2: Ag₂O; pyridine; molecular sieves 4 Angstroem / 16 h

3: aq. Na₂CO₃ / methanol / 2.5 h

With pyridine; 4 A molecular sieve; Imidazole hydrochloride; sodium carbonate; silver(l) oxide; In tetrahydrofuran; methanol;

DOI:10.1002/jms.1050

upstream raw materials:

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

2-(4-acetoxyphenyl)-5-hydroxy-4-oxochroman-7-yl acetate