((1S,5R)-1-Hydroxy-4-methyl-5-triisopropylsilanyloxy-cyclohex-3-enyl)-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrol-2-yl]-methanone

Base Information

• Chemical Name: ((1S,5R)-1-Hydroxy-4-methyl-5-triisopropylsilanyloxy-cyclohex-3-enyl)-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrol-2-yl]-methanone
• CAS No.: 852380-76-8
• Molecular Formula: C₂₇H₄₉NO₄Si₂
• Molecular Weight: 507.861
• Mol file: 852380-76-8.mol

Synonyms:((1S,5R)-1-Hydroxy-4-methyl-5-triisopropylsilanyloxy-cyclohex-3-enyl)-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrol-2-yl]-methanone

Chemical Property of ((1S,5R)-1-Hydroxy-4-methyl-5-triisopropylsilanyloxy-cyclohex-3-enyl)-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrol-2-yl]-methanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((1S,5R)-1-Hydroxy-4-methyl-5-triisopropylsilanyloxy-cyclohex-3-enyl)-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrol-2-yl]-methanone

There total 11 articles about ((1S,5R)-1-Hydroxy-4-methyl-5-triisopropylsilanyloxy-cyclohex-3-enyl)-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrol-2-yl]-methanone 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: 84.0%

((1S,5R)-1,5-Dihydroxy-4-methyl-cyclohex-3-enyl)-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrol-2-yl]-methanone (857287-66-2) + triisopropylsilyl trifluoromethanesulfonate (80522-42-5) → ((1S,5R)-1-Hydroxy-4-methyl-5-triisopropylsilanyloxy-cyclohex-3-enyl)-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrol-2-yl]-methanone (852380-76-8)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 23 ℃; for 0.0833333h;

DOI:10.1021/ja050586v

Reference yield:

(1R,5R,7R)-7-Hydroxy-6-methylene-1-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrole-2-carbonyl]-2,4-dioxa-bicyclo[3.3.1]nonan-3-one (852380-77-9) → ((1S,5R)-1-Hydroxy-4-methyl-5-triisopropylsilanyloxy-cyclohex-3-enyl)-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrol-2-yl]-methanone (852380-76-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / H₂ / Pd/C / methanol / 0.25 h / 0 °C

2: 84 percent / 2,6-lutidine / CH₂Cl₂ / 0.08 h / 23 °C

With 2,6-dimethylpyridine; hydrogen; palladium on activated charcoal; In methanol; dichloromethane;

DOI:10.1021/ja050586v

Reference yield:

[3-(tert-butyl-dimethyl-silanyloxy)-1,5-dihydroxy-4-methylene-cyclohexyl]-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrol-2-yl]-methanone (852380-57-5) → ((1S,5R)-1-Hydroxy-4-methyl-5-triisopropylsilanyloxy-cyclohex-3-enyl)-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrol-2-yl]-methanone (852380-76-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 92 percent / NaH / tetrahydrofuran / 0.33 h / 23 °C

2: 89 percent / TBAF / tetrahydrofuran / 0.05 h / 23 °C

3: 80 percent / H₂ / Pd/C / methanol / 0.25 h / 0 °C

4: 84 percent / 2,6-lutidine / CH₂Cl₂ / 0.08 h / 23 °C

With 2,6-dimethylpyridine; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/ja050586v

upstream raw materials:

((1S,5R)-1,5-Dihydroxy-4-methyl-cyclohex-3-enyl)-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrol-2-yl]-methanone

triisopropylsilyl trifluoromethanesulfonate

(1R,5R,7R)-7-Hydroxy-6-methylene-1-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrole-2-carbonyl]-2,4-dioxa-bicyclo[3.3.1]nonan-3-one

[3-(tert-butyl-dimethyl-silanyloxy)-1,5-dihydroxy-4-methylene-cyclohexyl]-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrol-2-yl]-methanone