Technology Process of (5R,6R,7R,8R)-6,7-Bis-benzyloxy-5-benzyloxymethyl-2-phenylethynyl-5,6,7,8-tetrahydro-imidazo[1,2-a]pyridin-8-ol
There total 15 articles about (5R,6R,7R,8R)-6,7-Bis-benzyloxy-5-benzyloxymethyl-2-phenylethynyl-5,6,7,8-tetrahydro-imidazo[1,2-a]pyridin-8-ol which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
tetrabutyl ammonium fluoride;
In
tetrahydrofuran;
at 20 ℃;
for 1h;
DOI:10.1021/ja066743n
- Guidance literature:
-
Multi-step reaction with 11 steps
1.1: n-BuLi / hexane; tetrahydrofuran / 0.5 h / -20 - 20 °C
1.2: tetrahydrofuran / 1 h / -78 - 20 °C
2.1: trifluoroacetic acid / CHCl3 / 0.42 h / 20 °C
3.1: 0.86 g / 4-N,N-dimethylaminopyridine; pyridine / 0.5 h / 20 °C
4.1: 90 percent / N-iodosuccinimide / acetonitrile / 12 h / 20 °C
5.1: 96 percent / aq. HCl / dioxane / 2 h / 20 °C
6.1: 89 percent / trifluoromethanesulfonic anhydride; pyridine / CH2Cl2 / -15 - 50 °C
7.1: sodium methoxide / CH2Cl2 / 0.17 h / 20 °C
8.1: 0.822 g / diisopropylethylamine / CH2Cl2 / 0.5 h / 0 - 20 °C
9.1: 93 percent / EtMgBr / tetrahydrofuran / 0.17 h / 0 °C
10.1: 96 percent / Et3N; CuI; Pd(PPh3)4 / dimethylformamide / 16 h / 80 °C
11.1: 76 percent / TBAF / tetrahydrofuran / 1 h / 20 °C
With
pyridine; hydrogenchloride; dmap; N-iodo-succinimide; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); n-butyllithium; ethylmagnesium bromide; tetrabutyl ammonium fluoride; sodium methylate; trifluoromethanesulfonic acid anhydride; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid;
In
tetrahydrofuran; 1,4-dioxane; hexane; dichloromethane; chloroform; N,N-dimethyl-formamide; acetonitrile;
10.1: Sonogashira coupling;
DOI:10.1021/ja066743n
- Guidance literature:
-
Multi-step reaction with 12 steps
1.1: 93 percent / oxalyl chloride; DMSO; Et3N / CH2Cl2 / 1 h / -60 - 0 °C
2.1: n-BuLi / hexane; tetrahydrofuran / 0.5 h / -20 - 20 °C
2.2: tetrahydrofuran / 1 h / -78 - 20 °C
3.1: trifluoroacetic acid / CHCl3 / 0.42 h / 20 °C
4.1: 0.86 g / 4-N,N-dimethylaminopyridine; pyridine / 0.5 h / 20 °C
5.1: 90 percent / N-iodosuccinimide / acetonitrile / 12 h / 20 °C
6.1: 96 percent / aq. HCl / dioxane / 2 h / 20 °C
7.1: 89 percent / trifluoromethanesulfonic anhydride; pyridine / CH2Cl2 / -15 - 50 °C
8.1: sodium methoxide / CH2Cl2 / 0.17 h / 20 °C
9.1: 0.822 g / diisopropylethylamine / CH2Cl2 / 0.5 h / 0 - 20 °C
10.1: 93 percent / EtMgBr / tetrahydrofuran / 0.17 h / 0 °C
11.1: 96 percent / Et3N; CuI; Pd(PPh3)4 / dimethylformamide / 16 h / 80 °C
12.1: 76 percent / TBAF / tetrahydrofuran / 1 h / 20 °C
With
pyridine; hydrogenchloride; dmap; N-iodo-succinimide; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); n-butyllithium; oxalyl dichloride; ethylmagnesium bromide; tetrabutyl ammonium fluoride; sodium methylate; dimethyl sulfoxide; trifluoromethanesulfonic acid anhydride; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid;
In
tetrahydrofuran; 1,4-dioxane; hexane; dichloromethane; chloroform; N,N-dimethyl-formamide; acetonitrile;
1.1: Swern oxidation / 11.1: Sonogashira coupling;
DOI:10.1021/ja066743n
![6,7-bis-benzyloxy-5-benzyloxymethyl-8-(<i>tert</i>-butyl-dimethyl-silanyloxy)-2-phenylethynyl-5,6,7,8-tetrahydro-imidazo[1,2-<i>a</i>]pyridine](/Databaselist/images/loading.webp)
