tert-Butyl-[(2S,4S)-4-(6-methoxy-5-methoxymethoxy-7-methyl-benzofuran-2-yl)-2-methyl-pentyloxy]-diphenyl-silane

Base Information

• Chemical Name: tert-Butyl-[(2S,4S)-4-(6-methoxy-5-methoxymethoxy-7-methyl-benzofuran-2-yl)-2-methyl-pentyloxy]-diphenyl-silane
• CAS No.: 638188-69-9
• Molecular Formula: C₃₄H₄₄O₅Si
• Molecular Weight: 560.806

Synonyms:tert-Butyl-[(2S,4S)-4-(6-methoxy-5-methoxymethoxy-7-methyl-benzofuran-2-yl)-2-methyl-pentyloxy]-diphenyl-silane

Chemical Property of tert-Butyl-[(2S,4S)-4-(6-methoxy-5-methoxymethoxy-7-methyl-benzofuran-2-yl)-2-methyl-pentyloxy]-diphenyl-silane

Chemical Property:

Purity/Quality:

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• Pictogram(s):  
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MSDS Files:

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Technology Process of tert-Butyl-[(2S,4S)-4-(6-methoxy-5-methoxymethoxy-7-methyl-benzofuran-2-yl)-2-methyl-pentyloxy]-diphenyl-silane

There total 14 articles about tert-Butyl-[(2S,4S)-4-(6-methoxy-5-methoxymethoxy-7-methyl-benzofuran-2-yl)-2-methyl-pentyloxy]-diphenyl-silane 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: 94.0%

chloromethyl methyl ether (107-30-2) + 2-[(1S,3S)-4-(tert-Butyl-diphenyl-silanyloxy)-1,3-dimethyl-butyl]-6-methoxy-7-methyl-benzofuran-5-ol (638188-68-8) → tert-Butyl-[(2S,4S)-4-(6-methoxy-5-methoxymethoxy-7-methyl-benzofuran-2-yl)-2-methyl-pentyloxy]-diphenyl-silane (638188-69-9)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 0.5h;

DOI:10.1021/ol035846x

Reference yield:

2-methoxy-3-methylbenzene-1,4-diol (1760-80-1) → tert-Butyl-[(2S,4S)-4-(6-methoxy-5-methoxymethoxy-7-methyl-benzofuran-2-yl)-2-methyl-pentyloxy]-diphenyl-silane (638188-69-9)

Guidance literature:

Multi-step reaction with 7 steps

1: NaH / dimethylformamide / 0.5 h / 0 °C

2: N-bromosuccinimide / CHCl₃ / 48 h / 5 °C

3: Mg / tetrahydrofuran / 2 h / Heating

4: 96 percent / CuI / 0.5 h / -30 °C

5: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

6: TfOH; MS 4 Angstroem / ethanol; toluene / 0.17 h / 80 °C

7: 94 percent / NaH / dimethylformamide / 0.5 h / 0 °C

With N-Bromosuccinimide; copper(l) iodide; oxalyl dichloride; trifluorormethanesulfonic acid; MS 4 Angstroem; sodium hydride; magnesium; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; ethanol; dichloromethane; chloroform; N,N-dimethyl-formamide; toluene; 5: Swern oxidation;

DOI:10.1021/ol035846x

Reference yield:

(R)-3-[(tert-butyldiphenylsilyl)oxy]-2-methylpropanal (91751-24-5,92817-88-4,123284-89-9,112897-04-8) → tert-Butyl-[(2S,4S)-4-(6-methoxy-5-methoxymethoxy-7-methyl-benzofuran-2-yl)-2-methyl-pentyloxy]-diphenyl-silane (638188-69-9)

Guidance literature:

Multi-step reaction with 9 steps

1.1: n-BuLi / H₂O; tetrahydrofuran

2.1: lithium tri-sec-butylborohydride / 2 h / -90 - -60 °C

2.2: hexamethylphosphoric triamide / 12 h / -78 °C

3.1: i-Bu₂AlH / 2 h / -78 °C

4.1: n-BuLi / 0 °C

5.1: m-chloroperbenzoic acid / CH₂Cl₂ / 20 °C

6.1: 96 percent / CuI / 0.5 h / -30 °C

7.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

8.1: TfOH; MS 4 Angstroem / ethanol; toluene / 0.17 h / 80 °C

9.1: 94 percent / NaH / dimethylformamide / 0.5 h / 0 °C

With copper(l) iodide; n-butyllithium; oxalyl dichloride; trifluorormethanesulfonic acid; MS 4 Angstroem; L-Selectride; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; 1.1: Horner-Wadsworth-Emmons olefination / 7.1: Swern oxidation;

DOI:10.1021/ol035846x

upstream raw materials:

chloromethyl methyl ether

2-[(1S,3S)-4-(tert-Butyl-diphenyl-silanyloxy)-1,3-dimethyl-butyl]-6-methoxy-7-methyl-benzofuran-5-ol

2-methoxy-3-methylbenzene-1,4-diol

(R)-3-[(tert-butyldiphenylsilyl)oxy]-2-methylpropanal

Downstream raw materials:

2-((2S,4S)-5-(tert-butyldiphenylsilyloxy)-4-methylpentan-2-yl)-4-((2R,3R,4S,5R,6R)-4-hydroxy-3,5-dimethyl-6-((S)-3-methylpent-4-enyl)tetrahydro-2H-pyran-2-yl)-6-methoxy-7-methylbenzofuran-5-ol

(2S)-1-(2-((2S,4S)-5-(tert-butyldiphenylsilyloxy)-4-methylpentan-2-yl)-6-methoxy-5-(methoxymethoxy)-7-methylbenzofuran-4-yl)-2-((4R,5S,6R)-2,2,5-trimethyl-6-((S)-3-methylpent-4-enyl)-1,3-dioxan-4-yl)propan-1-ol

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