(E)-(8R,9S)-11,11-Dibromo-7-(4-methoxy-benzyloxymethyl)-8-methoxymethoxy-9-methyl-undeca-6,10-dien-2-one

Base Information

• Chemical Name: (E)-(8R,9S)-11,11-Dibromo-7-(4-methoxy-benzyloxymethyl)-8-methoxymethoxy-9-methyl-undeca-6,10-dien-2-one
• CAS No.: 920753-31-7
• Molecular Formula: C₂₃H₃₂Br₂O₅
• Molecular Weight: 548.312
• Mol file: 920753-31-7.mol

Synonyms:

Chemical Property of (E)-(8R,9S)-11,11-Dibromo-7-(4-methoxy-benzyloxymethyl)-8-methoxymethoxy-9-methyl-undeca-6,10-dien-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(8R,9S)-11,11-Dibromo-7-(4-methoxy-benzyloxymethyl)-8-methoxymethoxy-9-methyl-undeca-6,10-dien-2-one

There total 10 articles about (E)-(8R,9S)-11,11-Dibromo-7-(4-methoxy-benzyloxymethyl)-8-methoxymethoxy-9-methyl-undeca-6,10-dien-2-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:

(4S,5S)-4-Hydroxy-5-(4-methoxy-benzyloxymethyl)-dihydro-furan-2-one → (E)-(8R,9S)-11,11-Dibromo-7-(4-methoxy-benzyloxymethyl)-8-methoxymethoxy-9-methyl-undeca-6,10-dien-2-one (920753-31-7)

Guidance literature:

Multi-step reaction with 8 steps

1.1: LDA / tetrahydrofuran / 6 h / -78 - 20 °C

2.1: i-Pr₂NEt / acetonitrile / 4 h / 50 °C

2.2: 85 percent / LAH / tetrahydrofuran / 0.5 h / 0 °C

3.1: Et₃N / 1,2-dichloro-ethane / 12 h / 50 °C

3.2: 90 percent / IBX / toluene; dimethylsulfoxide / 0.5 h / 50 °C

4.1: 65 percent / t-BuLi / tetrahydrofuran / 1 h / -78 - 20 °C

5.1: 75 percent / BF₃OEt₂ / CH₂Cl₂ / 1 h / 0 °C

6.1: PdCl₂ / dimethylformamide; H₂O / 12 h / 0 °C

7.1: IBX / toluene; dimethylsulfoxide / 3 h / 50 °C

8.1: PPh₃ / CH₂Cl₂ / 0.17 h / 0 °C

With boron trifluoride diethyl etherate; tert.-butyl lithium; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium diisopropyl amide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; palladium dichloride; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; acetonitrile; 6.1: Wacker oxidation;

DOI:10.1016/j.tetlet.2006.01.140

Reference yield:

(3R,4S,5S)-4-Hydroxy-5-(4-methoxy-benzyloxymethyl)-3-methyl-dihydro-furan-2-one → (E)-(8R,9S)-11,11-Dibromo-7-(4-methoxy-benzyloxymethyl)-8-methoxymethoxy-9-methyl-undeca-6,10-dien-2-one (920753-31-7)

Guidance literature:

Multi-step reaction with 7 steps

1.1: i-Pr₂NEt / acetonitrile / 4 h / 50 °C

1.2: 85 percent / LAH / tetrahydrofuran / 0.5 h / 0 °C

2.1: Et₃N / 1,2-dichloro-ethane / 12 h / 50 °C

2.2: 90 percent / IBX / toluene; dimethylsulfoxide / 0.5 h / 50 °C

3.1: 65 percent / t-BuLi / tetrahydrofuran / 1 h / -78 - 20 °C

4.1: 75 percent / BF₃OEt₂ / CH₂Cl₂ / 1 h / 0 °C

5.1: PdCl₂ / dimethylformamide; H₂O / 12 h / 0 °C

6.1: IBX / toluene; dimethylsulfoxide / 3 h / 50 °C

7.1: PPh₃ / CH₂Cl₂ / 0.17 h / 0 °C

With boron trifluoride diethyl etherate; tert.-butyl lithium; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; palladium dichloride; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; acetonitrile; 5.1: Wacker oxidation;

DOI:10.1016/j.tetlet.2006.01.140

Reference yield:

(2S,3R,4S)-5-(4-Methoxy-benzyloxy)-3-methoxymethoxy-2-methyl-pentane-1,4-diol (885218-85-9) → (E)-(8R,9S)-11,11-Dibromo-7-(4-methoxy-benzyloxymethyl)-8-methoxymethoxy-9-methyl-undeca-6,10-dien-2-one (920753-31-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: Et₃N / 1,2-dichloro-ethane / 12 h / 50 °C

1.2: 90 percent / IBX / toluene; dimethylsulfoxide / 0.5 h / 50 °C

2.1: 65 percent / t-BuLi / tetrahydrofuran / 1 h / -78 - 20 °C

3.1: 75 percent / BF₃OEt₂ / CH₂Cl₂ / 1 h / 0 °C

4.1: PdCl₂ / dimethylformamide; H₂O / 12 h / 0 °C

5.1: IBX / toluene; dimethylsulfoxide / 3 h / 50 °C

6.1: PPh₃ / CH₂Cl₂ / 0.17 h / 0 °C

With boron trifluoride diethyl etherate; tert.-butyl lithium; triethylamine; triphenylphosphine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; palladium dichloride; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; 4.1: Wacker oxidation;

DOI:10.1016/j.tetlet.2006.01.140

upstream raw materials:

carbon tetrabromide

(2S,3R,4S)-5-(4-Methoxy-benzyloxy)-3-methoxymethoxy-2-methyl-pentane-1,4-diol

(E)-(2S,3R)-4-(4-Methoxy-benzyloxymethyl)-3-methoxymethoxy-2-methyl-deca-4,9-dien-1-ol

(3R,4S)-1-(4-Methoxy-benzyloxy)-3-methoxymethoxy-4-methyl-5-trityloxy-pentan-2-one

Downstream raw materials:

(E)-(2R,8R,9S)-11,11-Dibromo-7-(4-methoxy-benzyloxymethyl)-8-methoxymethoxy-9-methyl-undeca-6,10-dien-2-ol

(E)-(2R,8R,9S)-7-(4-Methoxy-benzyloxymethyl)-8-methoxymethoxy-9-methyl-undec-6-en-10-yn-2-ol

C₂₃H₃₇BO₇

(7E,9E,13E)-(3S,4R,4aR,6aS,11S,12R,18R,20aR,20bS)-4-Hydroxy-13-(4-methoxy-benzyloxymethyl)-12-methoxymethoxy-3,6,11,18,20a-pentamethyl-1,2,3,4,4a,6a,11,12,15,16,17,18,20a,20b-tetradecahydro-19-oxa-cyclohexadeca[a]naphthalen-20-one