[2-((1S,3S)-4-Benzyloxy-1,3-dimethyl-butyl)-6-methoxy-7-methyl-benzofuran-5-yloxy]-tert-butyl-dimethyl-silane

Base Information

• Chemical Name: [2-((1S,3S)-4-Benzyloxy-1,3-dimethyl-butyl)-6-methoxy-7-methyl-benzofuran-5-yloxy]-tert-butyl-dimethyl-silane
• CAS No.: 808766-02-1
• Molecular Formula: C₂₉H₄₂O₄Si
• Molecular Weight: 482.736
• Mol file: 808766-02-1.mol

Synonyms:[2-((1S,3S)-4-Benzyloxy-1,3-dimethyl-butyl)-6-methoxy-7-methyl-benzofuran-5-yloxy]-tert-butyl-dimethyl-silane

Chemical Property of [2-((1S,3S)-4-Benzyloxy-1,3-dimethyl-butyl)-6-methoxy-7-methyl-benzofuran-5-yloxy]-tert-butyl-dimethyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [2-((1S,3S)-4-Benzyloxy-1,3-dimethyl-butyl)-6-methoxy-7-methyl-benzofuran-5-yloxy]-tert-butyl-dimethyl-silane

There total 10 articles about [2-((1S,3S)-4-Benzyloxy-1,3-dimethyl-butyl)-6-methoxy-7-methyl-benzofuran-5-yloxy]-tert-butyl-dimethyl-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%

C23H28O4 (1064710-63-9) + tert-butyldimethylsilyl chloride (18162-48-6) → [2-((1S,3S)-4-Benzyloxy-1,3-dimethyl-butyl)-6-methoxy-7-methyl-benzofuran-5-yloxy]-tert-butyl-dimethyl-silane (808766-02-1)

Guidance literature:

With 1H-imidazole; In dichloromethane; for 2h; Inert atmosphere;

Reference yield:

[2-((2S,4S)-5-Benzyloxy-2,4-dimethyl-pentanoyloxy)-5-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-3-methyl-benzyl]-triphenyl-phosphonium; bromide → [2-((1S,3S)-4-Benzyloxy-1,3-dimethyl-butyl)-6-methoxy-7-methyl-benzofuran-5-yloxy]-tert-butyl-dimethyl-silane (808766-02-1)

Guidance literature:

With triethylamine; In toluene; for 0.5h; Heating;

DOI:10.1021/ja0447154

Reference yield:

(2R)-3-iodo-2-methylpropyl benzyl ether (90344-49-3) → [2-((1S,3S)-4-Benzyloxy-1,3-dimethyl-butyl)-6-methoxy-7-methyl-benzofuran-5-yloxy]-tert-butyl-dimethyl-silane (808766-02-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: lithium diisopropylamide; LiCl / tetrahydrofuran; hexane / 1.33 h / -78 - 23 °C

1.2: 92 percent / tetrahydrofuran; hexane / 12 h / 0 °C

2.1: 83 percent / aq. tetra-n-butylammonium hydroxide / 2-methyl-propan-2-ol / 24 h / Heating

3.1: DCC; DMAP / CH₂Cl₂ / 12 h / 20 °C

4.1: 21 mg / Et₃N / toluene / 0.5 h / Heating

With dmap; tetra(n-butyl)ammonium hydroxide; triethylamine; dicyclohexyl-carbodiimide; lithium chloride; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; toluene; tert-butyl alcohol; 4.1: Wittig olefination;

DOI:10.1021/ja0447154

upstream raw materials:

(2R)-3-iodo-2-methylpropyl benzyl ether

tert-butyldimethylsilyl chloride

2,5-dihydroxy-4-methoxy-3-methyl-benzaldehyde

(2S,4S)-5-Benzyloxy-2,4-dimethyl-pentanoic acid

Downstream raw materials:

(5R,6R,7S,8R,9R,12S,13E,16S,18S,19S)-6,7,8,9,10,11,12,15,16,17,18,19-dodecahydro-4,7,19-trihydroxy-2,6,8,12,14,16,18-heptamethyl-1,19:5,9-diepoxybenzo[18]annulen-3(5H)-one