(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

Base Information

• Chemical Name: (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
• CAS No.: 911433-05-1
• Molecular Formula: C₃₁H₃₀F₆O₅
• Molecular Weight: 596.567

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 11 articles about (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 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: 92.0%

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) → (1S,5R,7R,8S)-7-Benzyloxymethyl-8-(2,6-bis-trifluoromethyl-benzyloxymethyl)-7,8,11-trimethyl-2-oxa-tricyclo[3.3.3.01,5]undec-10-ene-3,6-dione (911433-05-1)

Guidance literature:

With formic acid; tributyl-amine; triphenylphosphine; palladium diacetate; In N,N-dimethyl-formamide; at 40 ℃; for 2h;

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,5R,7R,8S)-7-Benzyloxymethyl-8-(2,6-bis-trifluoromethyl-benzyloxymethyl)-7,8,11-trimethyl-2-oxa-tricyclo[3.3.3.01,5]undec-10-ene-3,6-dione (911433-05-1)

Guidance literature:

Multi-step reaction with 11 steps

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

2.1: 75 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 3 h / 20 °C

3.1: 92 percent / o-iodoxybenzoic acid / dimethylsulfoxide / 1 h / 20 °C

4.1: 5.43 g / N,N-dimethylaniline / CH₂Cl₂ / 24 h / 0 - 20 °C

5.1: 17 percent / Bu₃SnH; 2,2'-azobisisobutyronitrile / toluene / 1 h / 85 °C

6.1: 72 percent / EtOTMS; BF₃*Et₂O / CH₂Cl₂ / 14 h / 40 °C

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

8.1: acetonitrile / 17 h / 20 °C

8.2: 61.4 mg / m-chloroperbenzoic acid / CH₂Cl₂ / 1 h / 20 °C

9.1: 100 percent / m-chloroperbenzoic acid; BF₃*Et₂O / CH₂Cl₂ / 0.17 h / 20 °C

10.1: 73 percent / LiBH(sBu)3; molecular sieves 4 Angstroem; L-Selectride / tetrahydrofuran / 0.67 h / -78 °C

11.1: 92 percent / tributylamine; PPh₃; formic acid / Pd(OAc)2 / dimethylformamide / 2 h / 40 °C

With formic acid; tributyl-amine; 2,2'-azobis(isobutyronitrile); ethyl trimethylsilyl ether; 4 A molecular sieve; boron trifluoride diethyl etherate; tri-n-butyl-tin hydride; potassium hexamethylsilazane; L-Selectride; N,N-dimethyl-aniline; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; palladium diacetate; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1002/anie.200601358

Reference yield:

(7R,8S)-7-Benzyloxymethyl-8-(2,6-bis-trifluoromethyl-benzyloxymethyl)-7,8-dimethyl-bicyclo[4.2.0]oct-3-ene-1,6-diol → (1S,5R,7R,8S)-7-Benzyloxymethyl-8-(2,6-bis-trifluoromethyl-benzyloxymethyl)-7,8,11-trimethyl-2-oxa-tricyclo[3.3.3.01,5]undec-10-ene-3,6-dione (911433-05-1)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 910 mg / Pb(OAc)4 / CH₂Cl₂ / 20 °C

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

3.1: 75 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 3 h / 20 °C

4.1: 92 percent / o-iodoxybenzoic acid / dimethylsulfoxide / 1 h / 20 °C

5.1: 5.43 g / N,N-dimethylaniline / CH₂Cl₂ / 24 h / 0 - 20 °C

6.1: 17 percent / Bu₃SnH; 2,2'-azobisisobutyronitrile / toluene / 1 h / 85 °C

7.1: 72 percent / EtOTMS; BF₃*Et₂O / CH₂Cl₂ / 14 h / 40 °C

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

9.1: acetonitrile / 17 h / 20 °C

9.2: 61.4 mg / m-chloroperbenzoic acid / CH₂Cl₂ / 1 h / 20 °C

10.1: 100 percent / m-chloroperbenzoic acid; BF₃*Et₂O / CH₂Cl₂ / 0.17 h / 20 °C

11.1: 73 percent / LiBH(sBu)3; molecular sieves 4 Angstroem; L-Selectride / tetrahydrofuran / 0.67 h / -78 °C

12.1: 92 percent / tributylamine; PPh₃; formic acid / Pd(OAc)2 / dimethylformamide / 2 h / 40 °C

With lead(IV) acetate; formic acid; tributyl-amine; 2,2'-azobis(isobutyronitrile); ethyl trimethylsilyl ether; 4 A molecular sieve; boron trifluoride diethyl etherate; tri-n-butyl-tin hydride; potassium hexamethylsilazane; L-Selectride; N,N-dimethyl-aniline; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; palladium diacetate; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1002/anie.200601358

upstream 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

(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

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