(1R,8R,9R,12S)-10-Oxo-8-phenyl-11-oxa-tricyclo[7.2.1.0^2,7]dodeca-2⁽⁷⁾,3,5-triene-12-carboxylic acid (S)-1-methoxycarbonyl-ethyl ester

Base Information

• Chemical Name: (1R,8R,9R,12S)-10-Oxo-8-phenyl-11-oxa-tricyclo[7.2.1.0^2,7]dodeca-2⁽⁷⁾,3,5-triene-12-carboxylic acid (S)-1-methoxycarbonyl-ethyl ester
• CAS No.: 130975-97-2
• Molecular Formula: C₂₂H₂₀O₆
• Molecular Weight: 380.397

Synonyms:(1R,8R,9R,12S)-10-Oxo-8-phenyl-11-oxa-tricyclo[7.2.1.0^2,7]dodeca-2⁽⁷⁾,3,5-triene-12-carboxylic acid (S)-1-methoxycarbonyl-ethyl ester

Chemical Property of (1R,8R,9R,12S)-10-Oxo-8-phenyl-11-oxa-tricyclo[7.2.1.0^2,7]dodeca-2⁽⁷⁾,3,5-triene-12-carboxylic acid (S)-1-methoxycarbonyl-ethyl ester

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Technology Process of (1R,8R,9R,12S)-10-Oxo-8-phenyl-11-oxa-tricyclo[7.2.1.0^2,7]dodeca-2⁽⁷⁾,3,5-triene-12-carboxylic acid (S)-1-methoxycarbonyl-ethyl ester

There total 3 articles about (1R,8R,9R,12S)-10-Oxo-8-phenyl-11-oxa-tricyclo[7.2.1.0^2,7]dodeca-2⁽⁷⁾,3,5-triene-12-carboxylic acid (S)-1-methoxycarbonyl-ethyl 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: 51.0%

(S)-Methyl lactate (-)-1-hydroxy-4-phenyl-1,2,3,4-tetrahydronaphthalene-2,3-dicarboxylate (130975-96-1) → (1R,8R,9R,12S)-10-Oxo-8-phenyl-11-oxa-tricyclo[7.2.1.02,7]dodeca-2(7),3,5-triene-12-carboxylic acid (S)-1-methoxycarbonyl-ethyl ester (130975-97-2)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; 1) 15 min, -78 deg C 2) 0.5 h, r.t.;

DOI:10.1139/v90-309

Reference yield:

2-benzylbenzaldehyde (32832-95-4) → (1R,8R,9R,12S)-10-Oxo-8-phenyl-11-oxa-tricyclo[7.2.1.02,7]dodeca-2(7),3,5-triene-12-carboxylic acid (S)-1-methoxycarbonyl-ethyl ester (130975-97-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 69 percent / SO₂ / benzene / 20 h / Irradiation; water-cooling

2: 54 percent / ZnO / CH₂Cl₂; toluene / 0.33 h / Heating

3: 51 percent / n-BuLi / hexane; tetrahydrofuran / 1) 15 min, -78 deg C 2) 0.5 h, r.t.

With n-butyllithium; sulfur dioxide; zinc(II) oxide; In tetrahydrofuran; hexane; dichloromethane; toluene; benzene;

DOI:10.1139/v90-309

Reference yield:

1-Hydroxy-3-phenyl-1,3-dihydrobenzothiophene 2,2-dioxide (92912-34-0,92912-38-4,95539-05-2,98678-31-0,98678-47-8) → (1R,8R,9R,12S)-10-Oxo-8-phenyl-11-oxa-tricyclo[7.2.1.02,7]dodeca-2(7),3,5-triene-12-carboxylic acid (S)-1-methoxycarbonyl-ethyl ester (130975-97-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 54 percent / ZnO / CH₂Cl₂; toluene / 0.33 h / Heating

2: 51 percent / n-BuLi / hexane; tetrahydrofuran / 1) 15 min, -78 deg C 2) 0.5 h, r.t.

With n-butyllithium; zinc(II) oxide; In tetrahydrofuran; hexane; dichloromethane; toluene;

DOI:10.1139/v90-309

upstream raw materials:

(S)-Methyl lactate (-)-1-hydroxy-4-phenyl-1,2,3,4-tetrahydronaphthalene-2,3-dicarboxylate

2-benzylbenzaldehyde

1-Hydroxy-3-phenyl-1,3-dihydrobenzothiophene 2,2-dioxide

Downstream raw materials:

(1R,2S,3R,4R)-1-Hydroxy-4-phenyl-1,2,3,4-tetrahydro-naphthalene-2,3-dicarboxylic acid 2-((S)-1-carboxy-ethyl) ester

(3aR,4R,9R,9aS)-9-Hydroxy-4-phenyl-3a,4,9,9a-tetrahydro-3H-naphtho[2,3-c]furan-1-one

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