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

Base Information

• Chemical Name: 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
• CAS No.: 911433-04-0
• Molecular Formula: C₃₂H₂₉F₉O₈S
• Molecular Weight: 744.629

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Technology Process of 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

There total 12 articles about 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 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%

(1S,5R,7R,8S)-7-Benzyloxymethyl-8-(2,6-bis-trifluoromethyl-benzyloxymethyl)-7,8-dimethyl-11-methylene-2-oxa-tricyclo[3.3.3.01,5]undecane-3,6,10-trione (911433-03-9) + N-(5-chloropyridin-2-yl)-1,1,1-trifluoro-N-[(trifluoromethyl)sulphonyl]methanesulphonamide (145100-51-2) → 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[3.3.3.01,5]undec-6-en-7-yl ester (911433-04-0)

Guidance literature:

With 4 A molecular sieve; L-Selectride; In tetrahydrofuran; at -78 ℃; for 0.666667h;

DOI:10.1002/anie.200601358

Reference yield:

(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 (911432-96-7) → 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[3.3.3.01,5]undec-6-en-7-yl ester (911433-04-0)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 92 percent / o-iodoxybenzoic acid / dimethylsulfoxide / 1 h / 20 °C

2.1: 5.43 g / N,N-dimethylaniline / CH₂Cl₂ / 24 h / 0 - 20 °C

3.1: 17 percent / Bu₃SnH; 2,2'-azobisisobutyronitrile / toluene / 1 h / 85 °C

4.1: 72 percent / EtOTMS; BF₃*Et₂O / CH₂Cl₂ / 14 h / 40 °C

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

6.1: acetonitrile / 17 h / 20 °C

6.2: 61.4 mg / m-chloroperbenzoic acid / CH₂Cl₂ / 1 h / 20 °C

7.1: 100 percent / m-chloroperbenzoic acid; BF₃*Et₂O / CH₂Cl₂ / 0.17 h / 20 °C

8.1: 73 percent / LiBH(sBu)3; molecular sieves 4 Angstroem; L-Selectride / tetrahydrofuran / 0.67 h / -78 °C

With 2,2'-azobis(isobutyronitrile); ethyl trimethylsilyl ether; 4 A molecular sieve; boron trifluoride diethyl etherate; tri-n-butyl-tin hydride; L-Selectride; 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; acetonitrile;

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) → 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[3.3.3.01,5]undec-6-en-7-yl ester (911433-04-0)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 75 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 3 h / 20 °C

2.1: 92 percent / o-iodoxybenzoic acid / dimethylsulfoxide / 1 h / 20 °C

3.1: 5.43 g / N,N-dimethylaniline / CH₂Cl₂ / 24 h / 0 - 20 °C

4.1: 17 percent / Bu₃SnH; 2,2'-azobisisobutyronitrile / toluene / 1 h / 85 °C

5.1: 72 percent / EtOTMS; BF₃*Et₂O / CH₂Cl₂ / 14 h / 40 °C

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

7.1: acetonitrile / 17 h / 20 °C

7.2: 61.4 mg / m-chloroperbenzoic acid / CH₂Cl₂ / 1 h / 20 °C

8.1: 100 percent / m-chloroperbenzoic acid; BF₃*Et₂O / CH₂Cl₂ / 0.17 h / 20 °C

9.1: 73 percent / LiBH(sBu)3; molecular sieves 4 Angstroem; L-Selectride / tetrahydrofuran / 0.67 h / -78 °C

With 2,2'-azobis(isobutyronitrile); ethyl trimethylsilyl ether; 4 A molecular sieve; boron trifluoride diethyl etherate; tri-n-butyl-tin hydride; L-Selectride; 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; acetonitrile;

DOI:10.1002/anie.200601358

upstream 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

N-(5-chloropyridin-2-yl)-1,1,1-trifluoro-N-[(trifluoromethyl)sulphonyl]methanesulphonamide

(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)-7,8,11-trimethyl-2-oxa-tricyclo[3.3.3.0^1,5]undec-10-ene-3,6-dione

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