4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-6-[2,6,12-tris-(tert-butyl-dimethyl-silanyloxy)-14-(4-methoxy-benzyloxy)-5,7,11,13,15-pentamethyl-nonadeca-3,8,16-trienyl]-tetrahydro-pyran-2-one

Base Information

• Chemical Name: 4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-6-[2,6,12-tris-(tert-butyl-dimethyl-silanyloxy)-14-(4-methoxy-benzyloxy)-5,7,11,13,15-pentamethyl-nonadeca-3,8,16-trienyl]-tetrahydro-pyran-2-one
• CAS No.: 837383-54-7
• Molecular Formula: C₆₃H₁₁₈O₈Si₄
• Molecular Weight: 1115.97

Synonyms:4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-6-[2,6,12-tris-(tert-butyl-dimethyl-silanyloxy)-14-(4-methoxy-benzyloxy)-5,7,11,13,15-pentamethyl-nonadeca-3,8,16-trienyl]-tetrahydro-pyran-2-one

Chemical Property of 4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-6-[2,6,12-tris-(tert-butyl-dimethyl-silanyloxy)-14-(4-methoxy-benzyloxy)-5,7,11,13,15-pentamethyl-nonadeca-3,8,16-trienyl]-tetrahydro-pyran-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of 4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-6-[2,6,12-tris-(tert-butyl-dimethyl-silanyloxy)-14-(4-methoxy-benzyloxy)-5,7,11,13,15-pentamethyl-nonadeca-3,8,16-trienyl]-tetrahydro-pyran-2-one

There total 9 articles about 4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-6-[2,6,12-tris-(tert-butyl-dimethyl-silanyloxy)-14-(4-methoxy-benzyloxy)-5,7,11,13,15-pentamethyl-nonadeca-3,8,16-trienyl]-tetrahydro-pyran-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: 73.0%

5,11,15-tris-(tert-butyl-dimethyl-silanyloxy)-16-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-6-oxo-tetrahydro-pyran-2-yl]-3-(4-methoxy-benzyloxy)-2,4,6,10,12-pentamethyl-hexadeca-8,13-dienal (837383-25-2) + n-propyltriphenylphosphonium bromide (6228-47-3) → 4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-6-[2,6,12-tris-(tert-butyl-dimethyl-silanyloxy)-14-(4-methoxy-benzyloxy)-5,7,11,13,15-pentamethyl-nonadeca-3,8,16-trienyl]-tetrahydro-pyran-2-one (837383-54-7)

Guidance literature:

n-propyltriphenylphosphonium bromide; With n-butyllithium; In tetrahydrofuran; at -78 - 40 ℃;

5,11,15-tris-(tert-butyl-dimethyl-silanyloxy)-16-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-6-oxo-tetrahydro-pyran-2-yl]-3-(4-methoxy-benzyloxy)-2,4,6,10,12-pentamethyl-hexadeca-8,13-dienal; In tetrahydrofuran; at 0 ℃; for 0.5h;

DOI:10.1021/ol0476873

Reference yield:

tert-Butyl-{(Z)-(1R,2S)-4-iodo-1-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2-methyl-but-3-enyloxy}-dimethyl-silane → 4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-6-[2,6,12-tris-(tert-butyl-dimethyl-silanyloxy)-14-(4-methoxy-benzyloxy)-5,7,11,13,15-pentamethyl-nonadeca-3,8,16-trienyl]-tetrahydro-pyran-2-one (837383-54-7)

Guidance literature:

Multi-step reaction with 8 steps

1.1: ZnCl₂; t-BuLi / diethyl ether; pentane / 1 h / 20 °C

1.2: 60 percent / Pd(PPh₃)4 / diethyl ether; pentane / 20 °C

2.1: 80 percent / H₂O; DDQ / CH₂Cl₂ / 1 h / 0 °C

3.1: 90 percent / PPh₃; imidazole; I₂ / benzene; diethyl ether / 0 - 20 °C

4.1: 82 percent / i-Pr₂NEt / 36 h / 100 °C

5.1: sodium bis(trimethylsilyl)amide / tetrahydrofuran / 0.75 h / -20 - 0 °C

5.2: 31 percent / tetrahydrofuran / 3 h / -20 - -8 °C

6.1: DIBAL-H / CH₂Cl₂ / 0.33 h / 20 °C

7.1: 145 mg / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 2.5 h / 0 °C

8.1: n-BuLi / tetrahydrofuran / -78 - 40 °C

8.2: 73 percent / tetrahydrofuran / 0.5 h / 0 °C

With 1H-imidazole; n-butyllithium; water; iodine; tert.-butyl lithium; sodium hexamethyldisilazane; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; zinc(II) chloride; In tetrahydrofuran; diethyl ether; dichloromethane; pentane; benzene; 7.1: Dess-Martin oxidation / 8.2: Wittig reaction;

DOI:10.1021/ol0476873

Reference yield:

(Z)-(2S,3R,4S,8S,9R,10R)-3,9-Bis-(tert-butyl-dimethyl-silanyloxy)-10-[(2S,4S,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-2,4,8-trimethyl-undec-5-en-1-ol (835929-77-6) → 4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-6-[2,6,12-tris-(tert-butyl-dimethyl-silanyloxy)-14-(4-methoxy-benzyloxy)-5,7,11,13,15-pentamethyl-nonadeca-3,8,16-trienyl]-tetrahydro-pyran-2-one (837383-54-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 90 percent / PPh₃; imidazole; I₂ / benzene; diethyl ether / 0 - 20 °C

2.1: 82 percent / i-Pr₂NEt / 36 h / 100 °C

3.1: sodium bis(trimethylsilyl)amide / tetrahydrofuran / 0.75 h / -20 - 0 °C

3.2: 31 percent / tetrahydrofuran / 3 h / -20 - -8 °C

4.1: DIBAL-H / CH₂Cl₂ / 0.33 h / 20 °C

5.1: 145 mg / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 2.5 h / 0 °C

6.1: n-BuLi / tetrahydrofuran / -78 - 40 °C

6.2: 73 percent / tetrahydrofuran / 0.5 h / 0 °C

With 1H-imidazole; n-butyllithium; iodine; sodium hexamethyldisilazane; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; diethyl ether; dichloromethane; benzene; 5.1: Dess-Martin oxidation / 6.2: Wittig reaction;

DOI:10.1021/ol0476873

upstream raw materials:

5,11,15-tris-(tert-butyl-dimethyl-silanyloxy)-16-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-6-oxo-tetrahydro-pyran-2-yl]-3-(4-methoxy-benzyloxy)-2,4,6,10,12-pentamethyl-hexadeca-8,13-dienal

n-propyltriphenylphosphonium bromide

(Z)-(2S,3R,4S,8S,9R,10R)-3,9-Bis-(tert-butyl-dimethyl-silanyloxy)-10-[(2S,4S,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-2,4,8-trimethyl-undec-5-en-1-ol

(2S,4S,5S)-4-[(Z)-(1R,2R,3S,7S,8R,9R)-2,8-Bis-(tert-butyl-dimethyl-silanyloxy)-10-iodo-1,3,7,9-tetramethyl-dec-5-enyl]-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxane

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