(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

Base Information

• Chemical Name: (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
• CAS No.: 911433-01-7
• Molecular Formula: C₃₅H₄₂F₆O₆Si
• Molecular Weight: 700.791

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

Useful:

Technology Process of (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

There total 9 articles about (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 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:

(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) + trimethylsilyl trifluoromethanesulfonate (27607-77-8) → (1S,3R,5R,7R,8S)-7-Benzyloxymethyl-8-(2,6-bis-trifluoromethyl-benzyloxymethyl)-3-ethoxy-7,8-dimethyl-10-trimethylsilanyloxy-2-oxa-tricyclo[3.3.3.01,5]undec-10-en-6-one (911433-01-7)

Guidance literature:

With triethylamine; In dichloromethane; at -20 ℃; for 2h;

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,3R,5R,7R,8S)-7-Benzyloxymethyl-8-(2,6-bis-trifluoromethyl-benzyloxymethyl)-3-ethoxy-7,8-dimethyl-10-trimethylsilanyloxy-2-oxa-tricyclo[3.3.3.01,5]undec-10-en-6-one (911433-01-7)

Guidance literature:

Multi-step reaction with 6 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

5: 72 percent / EtOTMS; BF₃*Et₂O / CH₂Cl₂ / 14 h / 40 °C

6: triethylamine / CH₂Cl₂ / 2 h / -20 °C

With 2,2'-azobis(isobutyronitrile); ethyl trimethylsilyl ether; boron trifluoride diethyl etherate; tri-n-butyl-tin hydride; N,N-dimethyl-aniline; triethylamine; 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

Reference yield:

(Z)-(2R,3S)-2-Benzyloxymethyl-3-(2,6-bis-trifluoromethyl-benzyloxymethyl)-2,3-dimethyl-cyclooct-6-ene-1,4-dione → (1S,3R,5R,7R,8S)-7-Benzyloxymethyl-8-(2,6-bis-trifluoromethyl-benzyloxymethyl)-3-ethoxy-7,8-dimethyl-10-trimethylsilanyloxy-2-oxa-tricyclo[3.3.3.01,5]undec-10-en-6-one (911433-01-7)

Guidance literature:

Multi-step reaction with 7 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

6: 72 percent / EtOTMS; BF₃*Et₂O / CH₂Cl₂ / 14 h / 40 °C

7: triethylamine / CH₂Cl₂ / 2 h / -20 °C

With 2,2'-azobis(isobutyronitrile); ethyl trimethylsilyl ether; boron trifluoride diethyl etherate; tri-n-butyl-tin hydride; potassium hexamethylsilazane; N,N-dimethyl-aniline; triethylamine; 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

upstream raw materials:

(1S,3R,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

trimethylsilyl trifluoromethanesulfonate

(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

Downstream raw materials:

(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

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-11-methylene-2-oxa-tricyclo[3.3.3.0^1,5]undecane-6,10-dione

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