(E)-3-(4-Acetoxy-3-methoxy-phenyl)-acrylic acid (3aR,5S,6S,7R,7aR)-7-acetoxy-2-cyano-2,5-dimethyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6-yl ester

Base Information

• Chemical Name: (E)-3-(4-Acetoxy-3-methoxy-phenyl)-acrylic acid (3aR,5S,6S,7R,7aR)-7-acetoxy-2-cyano-2,5-dimethyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6-yl ester
• CAS No.: 1053245-66-1
• Molecular Formula: C₂₃H₂₅NO₁₀
• Molecular Weight: 475.452
• Mol file: 1053245-66-1.mol

Synonyms:

Chemical Property of (E)-3-(4-Acetoxy-3-methoxy-phenyl)-acrylic acid (3aR,5S,6S,7R,7aR)-7-acetoxy-2-cyano-2,5-dimethyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-3-(4-Acetoxy-3-methoxy-phenyl)-acrylic acid (3aR,5S,6S,7R,7aR)-7-acetoxy-2-cyano-2,5-dimethyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6-yl ester

There total 8 articles about (E)-3-(4-Acetoxy-3-methoxy-phenyl)-acrylic acid (3aR,5S,6S,7R,7aR)-7-acetoxy-2-cyano-2,5-dimethyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6-yl ester 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:

benzyl 4-O-acetyl-2,3-O-isopropylidine-α-L-rhamnopyranoside (73351-48-1) → (E)-3-(4-Acetoxy-3-methoxy-phenyl)-acrylic acid (3aR,5S,6S,7R,7aR)-7-acetoxy-2-cyano-2,5-dimethyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6-yl ester (1053245-66-1)

Guidance literature:

Multi-step reaction with 8 steps

1: H₂ / Pd-C / ethanol

2: pyridinium p-toluenesulfonate

3: NaOMe / methanol

4: pyridine

5: 80percent aq. AcOH / Ambient temperature

6: pyridine

7: HBr, AcOH / CHCl₃

8: xylene / Heating

With pyridine; hydrogen bromide; hydrogen; sodium methylate; pyridinium p-toluenesulfonate; acetic acid; palladium on activated charcoal; In methanol; ethanol; chloroform; xylene;

DOI:10.1248/cpb.41.1882

Reference yield:

4-O-acetyl-2,3-O-isopropylidene-L-rhamnopyranose → (E)-3-(4-Acetoxy-3-methoxy-phenyl)-acrylic acid (3aR,5S,6S,7R,7aR)-7-acetoxy-2-cyano-2,5-dimethyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6-yl ester (1053245-66-1)

Guidance literature:

Multi-step reaction with 7 steps

1: pyridinium p-toluenesulfonate

2: NaOMe / methanol

3: pyridine

4: 80percent aq. AcOH / Ambient temperature

5: pyridine

6: HBr, AcOH / CHCl₃

7: xylene / Heating

With pyridine; hydrogen bromide; sodium methylate; pyridinium p-toluenesulfonate; acetic acid; In methanol; chloroform; xylene;

DOI:10.1248/cpb.41.1882

Reference yield:

(3aR,6S,7S,7aR)-2,2,6-Trimethyl-4-(tetrahydro-pyran-2-yloxy)-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-ol → (E)-3-(4-Acetoxy-3-methoxy-phenyl)-acrylic acid (3aR,5S,6S,7R,7aR)-7-acetoxy-2-cyano-2,5-dimethyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6-yl ester (1053245-66-1)

Guidance literature:

Multi-step reaction with 5 steps

1: pyridine

2: 80percent aq. AcOH / Ambient temperature

3: pyridine

4: HBr, AcOH / CHCl₃

5: xylene / Heating

With pyridine; hydrogen bromide; acetic acid; In chloroform; xylene;

DOI:10.1248/cpb.41.1882

upstream raw materials:

silver(I) cyanide

benzyl 4-O-acetyl-2,3-O-isopropylidine-α-L-rhamnopyranoside