Acetic acid (1R,5R)-5-hydroxy-2-methyl-5-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrole-2-carbonyl]-cyclohex-2-enyl ester

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Chemical Name:Acetic acid (1R,5R)-5-hydroxy-2-methyl-5-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrole-2-carbonyl]-cyclohex-2-enyl ester
CAS No.:852380-72-4
Molecular Formula:C₂₀H₃₁NO₅Si
Molecular Weight:393.555
Hs Code.:

Synonyms:Acetic acid (1R,5R)-5-hydroxy-2-methyl-5-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrole-2-carbonyl]-cyclohex-2-enyl ester

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Chemical Property of Acetic acid (1R,5R)-5-hydroxy-2-methyl-5-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrole-2-carbonyl]-cyclohex-2-enyl ester

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Technology Process of Acetic acid (1R,5R)-5-hydroxy-2-methyl-5-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrole-2-carbonyl]-cyclohex-2-enyl ester

There total 12 articles about Acetic acid (1R,5R)-5-hydroxy-2-methyl-5-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrole-2-carbonyl]-cyclohex-2-enyl 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: 92.0%

: 852380-69-9
((1R,5R)-1,5-Dihydroxy-4-methyl-cyclohex-3-enyl)-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrol-2-yl]-methanone

: 108-24-7
acetic anhydride

: 852380-72-4
Acetic acid (1R,5R)-5-hydroxy-2-methyl-5-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrole-2-carbonyl]-cyclohex-2-enyl ester

Guidance literature:: With dmap; In dichloromethane; at 23 ℃; for 0.833333h;
DOI:10.1021/ja050586v

Reference yield:

: 852380-48-4
(1R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-4-methyl-cyclohex-3-enecarboxylic acid methyl ester

: 852380-72-4
Acetic acid (1R,5R)-5-hydroxy-2-methyl-5-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrole-2-carbonyl]-cyclohex-2-enyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 99 percent / H₂ / Pd/C / methanol / 7 h / 0 °C / 760 Torr

2: 93 percent / 1,1'-carbonyldiimidazole / CH₂Cl₂ / 23 °C

3: 71 percent / tetrahydrofuran / -78 - 0 °C

4: 96 percent / TBAF / tetrahydrofuran / 0.08 h / 23 °C

5: 92 percent / DMAP / CH₂Cl₂ / 0.83 h / 23 °C

With dmap; tetrabutyl ammonium fluoride; hydrogen; 1,1'-carbonyldiimidazole; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/ja050586v

Reference yield:

: 852380-64-4
(3R,5R)-5-[(tert-butyldimethylsilyl)oxy]-1,3-dihydroxy-4-methylene-cyclohexanecarboxylic acid methyl ester

: 852380-72-4
Acetic acid (1R,5R)-5-hydroxy-2-methyl-5-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrole-2-carbonyl]-cyclohex-2-enyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 98 percent / triethylamine; DMAP / CH₂Cl₂ / 0.17 h / 23 °C

2: 89 percent / Pd(P(t-Bu)3)2; N-methylmorpholine N-oxide; triethylsilane / tetrahydrofuran / 3.5 h / 70 °C

3: 99 percent / H₂ / Pd/C / methanol / 7 h / 0 °C / 760 Torr

4: 93 percent / 1,1'-carbonyldiimidazole / CH₂Cl₂ / 23 °C

5: 71 percent / tetrahydrofuran / -78 - 0 °C

6: 96 percent / TBAF / tetrahydrofuran / 0.08 h / 23 °C

7: 92 percent / DMAP / CH₂Cl₂ / 0.83 h / 23 °C

With triethylsilane; dmap; bis(tri-t-butylphosphine)palladium⁽⁰⁾; tetrabutyl ammonium fluoride; hydrogen; 4-methylmorpholine N-oxide; triethylamine; 1,1'-carbonyldiimidazole; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/ja050586v