(2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(4-((E)-3-hydroxyprop-1-en-1 -yl)-2,6-dimethoxyphenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Base Information

• Chemical Name: (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(4-((E)-3-hydroxyprop-1-en-1 -yl)-2,6-dimethoxyphenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate
• CAS No.: 203179-64-0
• Molecular Formula: C₂₅H₃₂O₁₃
• Molecular Weight: 540.521
• Mol file: 203179-64-0.mol

Synonyms:(2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(4-((E)-3-hydroxyprop-1-en-1 -yl)-2,6-dimethoxyphenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Chemical Property of (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(4-((E)-3-hydroxyprop-1-en-1 -yl)-2,6-dimethoxyphenoxy)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-(4-((E)-3-hydroxyprop-1-en-1 -yl)-2,6-dimethoxyphenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate

There total 13 articles about (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(4-((E)-3-hydroxyprop-1-en-1 -yl)-2,6-dimethoxyphenoxy)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: 95.0%

3,5-dimethoxy-4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-trans-cinnamaldehyde (203179-62-8) → (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(4-((E)-3-hydroxyprop-1-en-1 -yl)-2,6-dimethoxyphenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate (203179-64-0)

Guidance literature:

With sodium tetrahydroborate; In tetrahydrofuran; methanol; at 20 ℃; for 1.5h;

DOI:10.1055/s-1998-2009

Reference yield: 71.1%

Syringenin (20675-96-1,104330-63-4,537-33-7) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(4-((E)-3-hydroxyprop-1-en-1 -yl)-2,6-dimethoxyphenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate (203179-64-0)

Guidance literature:

Syringenin; With tetrabutylammomium bromide; potassium carbonate; In dichloromethane; water; at 20 ℃; for 0.166667h;

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide; In dichloromethane; water; at 20 ℃; for 5h; stereoselective reaction;

DOI:10.1016/j.carres.2020.108200

Reference yield: 45.8%

trans-sinapyl alcohol (20675-96-1) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(4-((E)-3-hydroxyprop-1-en-1 -yl)-2,6-dimethoxyphenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate (203179-64-0)

Guidance literature:

trans-sinapyl alcohol; With tetrabutylammomium bromide; potassium carbonate; In dichloromethane; water; at 20 ℃; for 0.166667h;

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide; In dichloromethane; water; at 20 ℃; for 5h;

DOI:10.1080/10286020.2017.1379511

upstream raw materials:

3,5-dimethoxy-4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-trans-cinnamaldehyde

D-glucose pentaacetate

3,5-dimethoxy-4-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)benzaldehyde

syringic aldehyde

Downstream raw materials:

syringin