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ChemicalBook CAS DataBase List GLIOTOXIN

GLIOTOXIN synthesis

12synthesis methods
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Yield:-

Steps:

Multi-step reaction with 10 steps
1.1: thiourea / methanol / 2 h / 25 °C / Inert atmosphere
2.1: triethylamine / dichloromethane / 1.5 h / 0 °C / Inert atmosphere
3.1: toluene / 3 h / 110 °C / Inert atmosphere
4.1: phosphorous acid trimethyl ester / 16 h / 111 °C / Inert atmosphere
5.1: hydrogenchloride / diethyl ether; dichloromethane / 0.25 h / 0 °C / Inert atmosphere
6.1: lithium hydroxide / tetrahydrofuran; water / 5 h / 0 - 25 °C
6.2: pH 3
7.1: 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / dichloromethane / 15 h / 0 - 25 °C / Inert atmosphere
8.1: dichloromethane / 3 h / 0 - 25 °C / Inert atmosphere
9.1: triethylamine / dichloromethane / 15 h / 0 - 25 °C / Inert atmosphere
10.1: sulfur; lithium hexamethyldisilazane / tetrahydrofuran / 2.08 h / 25 °C / Inert atmosphere

References:

Nicolaou, K. C.;Lu, Min;Totokotsopoulos, Sotirios;Heretsch, Philipp;Giguere, Denis;Sun, Ya-Ping;Sarlah, David;Nguyen, Thu H.;Wolf, Ian C.;Smee, Donald F.;Day, Craig W.;Bopp, Selina;Winzeler, Elizabeth A. [Journal of the American Chemical Society,2012,vol. 134,# 41,p. 17320 - 17332,13]

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