Acetic acid (1R,3R,5S)-3,5-dihydroxy-2-methylene-5-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrole-2-carbonyl]-cyclohexyl ester

Base Information

Chemical Name:Acetic acid (1R,3R,5S)-3,5-dihydroxy-2-methylene-5-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrole-2-carbonyl]-cyclohexyl ester
CAS No.:852380-79-1
Molecular Formula:C₂₀H₃₁NO₆Si
Molecular Weight:409.555
Hs Code.:

Synonyms:Acetic acid (1R,3R,5S)-3,5-dihydroxy-2-methylene-5-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrole-2-carbonyl]-cyclohexyl ester

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Chemical Property of Acetic acid (1R,3R,5S)-3,5-dihydroxy-2-methylene-5-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrole-2-carbonyl]-cyclohexyl ester

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Technology Process of Acetic acid (1R,3R,5S)-3,5-dihydroxy-2-methylene-5-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrole-2-carbonyl]-cyclohexyl ester

There total 7 articles about Acetic acid (1R,3R,5S)-3,5-dihydroxy-2-methylene-5-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrole-2-carbonyl]-cyclohexyl 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:

: acetic acid 3-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-2-methylene-5-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrole-2-carbonyl]-cyclohexyl ester

: 852380-79-1
Acetic acid (1R,3R,5S)-3,5-dihydroxy-2-methylene-5-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrole-2-carbonyl]-cyclohexyl ester

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 23 ℃; for 0.0333333h;
DOI:10.1021/ja050586v

Reference yield:

: 852380-68-8
[3-(tert-butyl-dimethyl-silanyloxy)-1,5-dihydroxy-4-methylene-cyclohexyl]-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrol-2-yl]-methanone

: 852380-79-1
Acetic acid (1R,3R,5S)-3,5-dihydroxy-2-methylene-5-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrole-2-carbonyl]-cyclohexyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: triethylamine; DMAP / CH₂Cl₂ / 0.25 h / 23 °C

2: 1.49 g / TBAF / tetrahydrofuran / 0.03 h / 23 °C

With dmap; tetrabutyl ammonium fluoride; triethylamine; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ja050586v

Reference yield:

: 77-95-2
D-(-)-quinic acid

: 852380-79-1
Acetic acid (1R,3R,5S)-3,5-dihydroxy-2-methylene-5-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrole-2-carbonyl]-cyclohexyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: Amberlyst H⁺ resin; benzene / dimethylformamide / Heating

2.1: triethylamine; DMAP / dimethylformamide / 23 °C

3.1: pyridinium dichromate; Celite; molecular sieves 4 Angstroem / acetonitrile / 45 °C

4.1: t-BuOK / tetrahydrofuran / 65 °C

5.1: n-BuLi / tetrahydrofuran; hexane / 0.12 h / -78 °C

5.2: 86 percent / tetrahydrofuran; hexane / 0.5 h / -42 °C

6.1: triethylamine; DMAP / CH₂Cl₂ / 0.25 h / 23 °C

7.1: 1.49 g / TBAF / tetrahydrofuran / 0.03 h / 23 °C

With dmap; dipyridinium dichromate; n-butyllithium; 4 A molecular sieve; Amberlyst H⁺ resin; Celite; potassium tert-butylate; tetrabutyl ammonium fluoride; triethylamine; benzene; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 4.1: Wittig olefination;
DOI:10.1021/ja050586v