(E)-3-((2R,4aR,6S,7R,9aS)-7-Hydroxy-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-6-yl)-acrylic acid methyl ester

Base Information

• Chemical Name: (E)-3-((2R,4aR,6S,7R,9aS)-7-Hydroxy-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-6-yl)-acrylic acid methyl ester
• CAS No.: 440333-72-2
• Molecular Formula: C₁₈H₂₂O₆
• Molecular Weight: 334.369

Synonyms:(E)-3-((2R,4aR,6S,7R,9aS)-7-Hydroxy-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-6-yl)-acrylic acid methyl ester

Chemical Property of (E)-3-((2R,4aR,6S,7R,9aS)-7-Hydroxy-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-6-yl)-acrylic acid methyl ester

Chemical Property:

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Technology Process of (E)-3-((2R,4aR,6S,7R,9aS)-7-Hydroxy-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-6-yl)-acrylic acid methyl ester

There total 2 articles about (E)-3-((2R,4aR,6S,7R,9aS)-7-Hydroxy-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-6-yl)-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:

(2R,4aR,6S,7R,9aS)-2-Phenyl-6-vinyl-hexahydro-1,3,5-trioxa-benzocyclohepten-7-ol (213815-32-8) → (E)-3-((2R,4aR,6S,7R,9aS)-7-Hydroxy-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-6-yl)-acrylic acid methyl ester (440333-72-2)

Guidance literature:

Multi-step reaction with 2 steps

1: O₃ / tetrahydrofuran / -78 °C

2: CH₂Cl₂ / 20 °C

With ozone; In tetrahydrofuran; dichloromethane; 2: Wittig reaction;

DOI:10.1016/j.tetlet.2007.03.041

Reference yield:

methyl (triphenylphosphoranylidene)acetate (21204-67-1,2605-67-6) + (2R,4aR,6R,7R,9aS)-7-Hydroxy-2-phenyl-hexahydro-1,3,5-trioxa-benzocycloheptene-6-carbaldehyde → (E)-3-((2R,4aR,6S,7R,9aS)-7-Hydroxy-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-6-yl)-acrylic acid methyl ester (440333-72-2)

Guidance literature:

In dichloromethane;

DOI:10.1016/S0040-4020(02)00039-X

Reference yield: 98.0%

(E)-3-((2R,4aR,6S,7R,9aS)-7-Hydroxy-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-6-yl)-acrylic acid methyl ester (440333-72-2) → 3-((2R,4aR,6S,7R,9aS)-7-Hydroxy-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-6-yl)-propionic acid methyl ester (440334-02-1)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; at 20 ℃;

DOI:10.1016/S0040-4020(02)00039-X

upstream raw materials:

methyl (triphenylphosphoranylidene)acetate

(2R,4aR,6S,7R,9aS)-2-Phenyl-6-vinyl-hexahydro-1,3,5-trioxa-benzocyclohepten-7-ol

Downstream raw materials:

3-((2R,4aR,6S,7R,9aS)-7-Hydroxy-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-6-yl)-propionic acid methyl ester

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