(E)-3-[3-Benzyloxy-4-((3aR,4S,6R,7S,7aS)-7-hydroxy-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-phenyl]-acrylic acid methyl ester

Base Information

• Chemical Name: (E)-3-[3-Benzyloxy-4-((3aR,4S,6R,7S,7aS)-7-hydroxy-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-phenyl]-acrylic acid methyl ester
• CAS No.: 868671-99-2
• Molecular Formula: C₂₆H₃₀O₈
• Molecular Weight: 470.519
• Mol file: 868671-99-2.mol

Synonyms:(E)-3-[3-Benzyloxy-4-((3aR,4S,6R,7S,7aS)-7-hydroxy-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-phenyl]-acrylic acid methyl ester

Chemical Property of (E)-3-[3-Benzyloxy-4-((3aR,4S,6R,7S,7aS)-7-hydroxy-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-phenyl]-acrylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-3-[3-Benzyloxy-4-((3aR,4S,6R,7S,7aS)-7-hydroxy-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-phenyl]-acrylic acid methyl ester

There total 4 articles about (E)-3-[3-Benzyloxy-4-((3aR,4S,6R,7S,7aS)-7-hydroxy-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-phenyl]-acrylic acid methyl 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: 98.0%

(E)-3-[3-Benzyloxy-4-((2R,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-phenyl]-acrylic acid methyl ester (868671-98-1) + 2,2-dimethoxy-propane (77-76-9) → (E)-3-[3-Benzyloxy-4-((3aR,4S,6R,7S,7aS)-7-hydroxy-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-phenyl]-acrylic acid methyl ester (868671-99-2)

Guidance literature:

With pyridinium p-toluenesulfonate; In acetone; at 20 ℃; for 6h;

DOI:10.1021/ol051971s

Reference yield:

3-benzyloxy-4-hydroxy-trans-cinnamic acid methyl ester (868671-93-6) → (E)-3-[3-Benzyloxy-4-((3aR,4S,6R,7S,7aS)-7-hydroxy-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-phenyl]-acrylic acid methyl ester (868671-99-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 80 percent / BF₃*Et₂O; 4 Angstroem molecular sieves / CH₂Cl₂ / 0.5 h / -78 °C

2: 79 percent / K₂CO₃ / methanol / 12 h / 20 °C

3: 98 percent / PPTS / acetone / 6 h / 20 °C

With 4 A molecular sieve; boron trifluoride diethyl etherate; pyridinium p-toluenesulfonate; potassium carbonate; In methanol; dichloromethane; acetone; 1: Schmidt glycosylation;

DOI:10.1021/ol051971s

Reference yield:

(E)-3-[3-Benzyloxy-4-((2R,3S,4R,5R,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-yloxy)-phenyl]-acrylic acid methyl ester (868671-95-8) → (E)-3-[3-Benzyloxy-4-((3aR,4S,6R,7S,7aS)-7-hydroxy-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-phenyl]-acrylic acid methyl ester (868671-99-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 79 percent / K₂CO₃ / methanol / 12 h / 20 °C

2: 98 percent / PPTS / acetone / 6 h / 20 °C

With pyridinium p-toluenesulfonate; potassium carbonate; In methanol; acetone;

DOI:10.1021/ol051971s

upstream raw materials:

(E)-3-[3-Benzyloxy-4-((2R,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-phenyl]-acrylic acid methyl ester

2,2-dimethoxy-propane

3-benzyloxy-4-hydroxy-trans-cinnamic acid methyl ester

(E)-3-[3-Benzyloxy-4-((2R,3S,4R,5R,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-yloxy)-phenyl]-acrylic acid methyl ester

Downstream raw materials:

(E)-3-[3-Benzyloxy-4-((3aR,4S,6R,7S,7aR)-2,2,4-trimethyl-7-sulfooxy-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-phenyl]-acrylic acid methyl ester