(1S,3S,5R,7R,8S)-7-Benzyloxymethyl-8-(2,6-bis-trifluoromethyl-benzyloxymethyl)-3-ethoxy-7,8-dimethyl-2-oxa-tricyclo[3.3.3.0^1,5]undecane-6,10-dione

Base Information

• Chemical Name: (1S,3S,5R,7R,8S)-7-Benzyloxymethyl-8-(2,6-bis-trifluoromethyl-benzyloxymethyl)-3-ethoxy-7,8-dimethyl-2-oxa-tricyclo[3.3.3.0^1,5]undecane-6,10-dione
• CAS No.: 911433-00-6
• Molecular Formula: C₃₂H₃₄F₆O₆
• Molecular Weight: 628.609

Synonyms:(1S,3S,5R,7R,8S)-7-Benzyloxymethyl-8-(2,6-bis-trifluoromethyl-benzyloxymethyl)-3-ethoxy-7,8-dimethyl-2-oxa-tricyclo[3.3.3.0^1,5]undecane-6,10-dione

Chemical Property of (1S,3S,5R,7R,8S)-7-Benzyloxymethyl-8-(2,6-bis-trifluoromethyl-benzyloxymethyl)-3-ethoxy-7,8-dimethyl-2-oxa-tricyclo[3.3.3.0^1,5]undecane-6,10-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,3S,5R,7R,8S)-7-Benzyloxymethyl-8-(2,6-bis-trifluoromethyl-benzyloxymethyl)-3-ethoxy-7,8-dimethyl-2-oxa-tricyclo[3.3.3.0^1,5]undecane-6,10-dione

There total 7 articles about (1S,3S,5R,7R,8S)-7-Benzyloxymethyl-8-(2,6-bis-trifluoromethyl-benzyloxymethyl)-3-ethoxy-7,8-dimethyl-2-oxa-tricyclo[3.3.3.0^1,5]undecane-6,10-dione 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: 73.0%

(2R,3S,3aS)-2-Benzyloxymethyl-3-(2,6-bis-trifluoromethyl-benzyloxymethyl)-3a-(2-bromo-1-ethoxy-ethoxy)-2,3-dimethyl-2,3,3a,4-tetrahydro-pentalene-1,5-dione (911432-98-9) → (1S,3S,5R,7R,8S)-7-Benzyloxymethyl-8-(2,6-bis-trifluoromethyl-benzyloxymethyl)-3-ethoxy-7,8-dimethyl-2-oxa-tricyclo[3.3.3.01,5]undecane-6,10-dione (911433-00-6) + (1S,3R,5R,7R,8S)-7-Benzyloxymethyl-8-(2,6-bis-trifluoromethyl-benzyloxymethyl)-3-ethoxy-7,8-dimethyl-2-oxa-tricyclo[3.3.3.01,5]undecane-6,10-dione (911432-99-0)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; at 85 ℃; for 1h;

DOI:10.1002/anie.200601358

Reference yield:

(Z)-(2R,3S)-2-Benzyloxymethyl-3-(2,6-bis-trifluoromethyl-benzyloxymethyl)-2,3-dimethyl-cyclooct-6-ene-1,4-dione → (1S,3S,5R,7R,8S)-7-Benzyloxymethyl-8-(2,6-bis-trifluoromethyl-benzyloxymethyl)-3-ethoxy-7,8-dimethyl-2-oxa-tricyclo[3.3.3.01,5]undecane-6,10-dione (911433-00-6)

Guidance literature:

Multi-step reaction with 5 steps

1: KN(TMS)2 / tetrahydrofuran / -100 °C

2: 75 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 3 h / 20 °C

3: 92 percent / o-iodoxybenzoic acid / dimethylsulfoxide / 1 h / 20 °C

4: 5.43 g / N,N-dimethylaniline / CH₂Cl₂ / 24 h / 0 - 20 °C

5: 17 percent / Bu₃SnH; 2,2'-azobisisobutyronitrile / toluene / 1 h / 85 °C

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; potassium hexamethylsilazane; N,N-dimethyl-aniline; 3-chloro-benzenecarboperoxoic acid; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; toluene;

DOI:10.1002/anie.200601358

Reference yield:

(2R,3S,3aR,6aR)-2-Benzyloxymethyl-3-(2,6-bis-trifluoromethyl-benzyloxymethyl)-3a-hydroxy-2,3-dimethyl-3,3a,4,6a-tetrahydro-2H-pentalen-1-one (911432-81-0) → (1S,3S,5R,7R,8S)-7-Benzyloxymethyl-8-(2,6-bis-trifluoromethyl-benzyloxymethyl)-3-ethoxy-7,8-dimethyl-2-oxa-tricyclo[3.3.3.01,5]undecane-6,10-dione (911433-00-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 75 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 3 h / 20 °C

2: 92 percent / o-iodoxybenzoic acid / dimethylsulfoxide / 1 h / 20 °C

3: 5.43 g / N,N-dimethylaniline / CH₂Cl₂ / 24 h / 0 - 20 °C

4: 17 percent / Bu₃SnH; 2,2'-azobisisobutyronitrile / toluene / 1 h / 85 °C

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; N,N-dimethyl-aniline; 3-chloro-benzenecarboperoxoic acid; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In dichloromethane; dimethyl sulfoxide; toluene;

DOI:10.1002/anie.200601358

upstream raw materials:

(2R,3S,3aS)-2-Benzyloxymethyl-3-(2,6-bis-trifluoromethyl-benzyloxymethyl)-3a-(2-bromo-1-ethoxy-ethoxy)-2,3-dimethyl-2,3,3a,4-tetrahydro-pentalene-1,5-dione

(2R,3S,3aR,6aR)-2-Benzyloxymethyl-3-(2,6-bis-trifluoromethyl-benzyloxymethyl)-3a-hydroxy-2,3-dimethyl-3,3a,4,6a-tetrahydro-2H-pentalen-1-one

(2R,3S,3aS,5S)-2-Benzyloxymethyl-3-(2,6-bis-trifluoromethyl-benzyloxymethyl)-3a,5-dihydroxy-2,3-dimethyl-3,3a,4,5-tetrahydro-2H-pentalen-1-one

(2R,3S,3aS)-2-Benzyloxymethyl-3-(2,6-bis-trifluoromethyl-benzyloxymethyl)-3a-hydroxy-2,3-dimethyl-2,3,3a,4-tetrahydro-pentalene-1,5-dione

Downstream raw materials:

Trifluoro-methanesulfonic acid (1S,5R,9S,10R)-10-benzyloxymethyl-9-(2,6-bis-trifluoromethyl-benzyloxymethyl)-6,9,10-trimethyl-3,11-dioxo-2-oxa-tricyclo[3.3.3.0^1,5]undec-6-en-7-yl ester

(1S,3R,5R,7R,8S)-7-Benzyloxymethyl-8-(2,6-bis-trifluoromethyl-benzyloxymethyl)-3-ethoxy-7,8-dimethyl-10-trimethylsilanyloxy-2-oxa-tricyclo[3.3.3.0^1,5]undec-10-en-6-one

(1S,3R,5R,7R,8S)-7-Benzyloxymethyl-8-(2,6-bis-trifluoromethyl-benzyloxymethyl)-3-ethoxy-7,8-dimethyl-11-methylene-2-oxa-tricyclo[3.3.3.0^1,5]undecane-6,10-dione

(1S,5R,7R,8S)-7-Benzyloxymethyl-8-(2,6-bis-trifluoromethyl-benzyloxymethyl)-7,8-dimethyl-11-methylene-2-oxa-tricyclo[3.3.3.0^1,5]undecane-3,6,10-trione

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