5-hydroxy-2-[12-hydroxy-7-(4-methoxy-benzyloxymethyl)-6-methoxymethoxy-5-methyl-trideca-1,3,7-trienyl]-1,3,6-trimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid 2-trimethylsilanyl-ethyl ester

Base Information

• Chemical Name: 5-hydroxy-2-[12-hydroxy-7-(4-methoxy-benzyloxymethyl)-6-methoxymethoxy-5-methyl-trideca-1,3,7-trienyl]-1,3,6-trimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid 2-trimethylsilanyl-ethyl ester
• CAS No.: 1027485-85-3
• Molecular Formula: C₄₄H₇₀O₈Si
• Molecular Weight: 755.12
• Mol file: 1027485-85-3.mol

Synonyms:5-hydroxy-2-[12-hydroxy-7-(4-methoxy-benzyloxymethyl)-6-methoxymethoxy-5-methyl-trideca-1,3,7-trienyl]-1,3,6-trimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid 2-trimethylsilanyl-ethyl ester

Chemical Property of 5-hydroxy-2-[12-hydroxy-7-(4-methoxy-benzyloxymethyl)-6-methoxymethoxy-5-methyl-trideca-1,3,7-trienyl]-1,3,6-trimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid 2-trimethylsilanyl-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-hydroxy-2-[12-hydroxy-7-(4-methoxy-benzyloxymethyl)-6-methoxymethoxy-5-methyl-trideca-1,3,7-trienyl]-1,3,6-trimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid 2-trimethylsilanyl-ethyl ester

There total 22 articles about 5-hydroxy-2-[12-hydroxy-7-(4-methoxy-benzyloxymethyl)-6-methoxymethoxy-5-methyl-trideca-1,3,7-trienyl]-1,3,6-trimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid 2-trimethylsilanyl-ethyl 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: 35.0%

(1R,2S,4aR,5R,6S,8aS)-5-Hydroxy-2-((E)-2-iodo-vinyl)-1,3,6-trimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid 2-trimethylsilanyl-ethyl ester (885218-83-7) + C23H37BO7 (885218-91-7) → 5-hydroxy-2-[12-hydroxy-7-(4-methoxy-benzyloxymethyl)-6-methoxymethoxy-5-methyl-trideca-1,3,7-trienyl]-1,3,6-trimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid 2-trimethylsilanyl-ethyl ester (1027485-85-3)

Guidance literature:

With triphenyl-arsane; thallium (I) ethoxide; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In tetrahydrofuran; water; at 20 ℃; for 0.166667h;

DOI:10.1016/j.tetlet.2006.01.140

Reference yield:

(4S,5S)-4-Hydroxy-5-(4-methoxy-benzyloxymethyl)-dihydro-furan-2-one → 5-hydroxy-2-[12-hydroxy-7-(4-methoxy-benzyloxymethyl)-6-methoxymethoxy-5-methyl-trideca-1,3,7-trienyl]-1,3,6-trimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid 2-trimethylsilanyl-ethyl ester (1027485-85-3)

Guidance literature:

Multi-step reaction with 12 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

9.1: (S)-CBS; catecholborane / tetrahydrofuran; CH₂Cl₂ / 8 h / -78 °C

10.1: n-BuLi / tetrahydrofuran / 0.17 h / 0 °C

11.1: 61 percent / catecholborane / tetrahydrofuran / 72 h / Heating

12.1: 35 percent / AsPh₃; TlOEt / Pd₂(dba)3 / tetrahydrofuran; H₂O / 0.17 h / 20 °C

With n-butyllithium; (S)-diphenylprolinol; triphenyl-arsane; boron trifluoride diethyl etherate; tert.-butyl lithium; thallium (I) ethoxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium diisopropyl amide; benzo[1,3,2]dioxaborole; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; palladium dichloride; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; acetonitrile; 6.1: Wacker oxidation / 12.1: Suzuki-Miyaura coupling;

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 → 5-hydroxy-2-[12-hydroxy-7-(4-methoxy-benzyloxymethyl)-6-methoxymethoxy-5-methyl-trideca-1,3,7-trienyl]-1,3,6-trimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid 2-trimethylsilanyl-ethyl ester (1027485-85-3)

Guidance literature:

Multi-step reaction with 11 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

8.1: (S)-CBS; catecholborane / tetrahydrofuran; CH₂Cl₂ / 8 h / -78 °C

9.1: n-BuLi / tetrahydrofuran / 0.17 h / 0 °C

10.1: 61 percent / catecholborane / tetrahydrofuran / 72 h / Heating

11.1: 35 percent / AsPh₃; TlOEt / Pd₂(dba)3 / tetrahydrofuran; H₂O / 0.17 h / 20 °C

With n-butyllithium; (S)-diphenylprolinol; triphenyl-arsane; boron trifluoride diethyl etherate; tert.-butyl lithium; thallium (I) ethoxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; benzo[1,3,2]dioxaborole; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; palladium dichloride; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; acetonitrile; 5.1: Wacker oxidation / 11.1: Suzuki-Miyaura coupling;

DOI:10.1016/j.tetlet.2006.01.140

upstream raw materials:

(1R,2S,4aR,5R,6S,8aS)-5-Hydroxy-2-((E)-2-iodo-vinyl)-1,3,6-trimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid 2-trimethylsilanyl-ethyl ester

C₂₃H₃₇BO₇

(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

Downstream raw materials:

(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

(1R,2S,4aR,5R,6S,8aS)-5-Hydroxy-2-[(1E,3E,7E)-(5S,6R,12R)-12-hydroxy-7-(4-methoxy-benzyloxymethyl)-6-methoxymethoxy-5-methyl-trideca-1,3,7-trienyl]-1,3,6-trimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid