Technology Process of (4S,4'R,6S)-4,6-diethyl-4-(4-ethyl-2-methylocta-1,5-dienyl)-2-phenyl-6-vinyl-1,3-dioxane
There total 15 articles about (4S,4'R,6S)-4,6-diethyl-4-(4-ethyl-2-methylocta-1,5-dienyl)-2-phenyl-6-vinyl-1,3-dioxane which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 4 steps
1.1: 95 percent / t-BuOK / tetrahydrofuran / 18 h / -55 - 23 °C
2.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C
2.2: 95 percent / tetrahydrofuran; hexane / 1 h / -78 °C
3.1: tricyclohexylphosphine; tributyltin hydride / Pd(OAc)2 / hexane / 15 h / -35 °C
3.2: 29 percent / N-iodosuccinimide / tetrahydrofuran / 2 h / 0 °C
4.1: t-BuLi; 9-methoxy-9-borabicyclo[3.3.1]nonane / diethyl ether; pentane; tetrahydrofuran / -78 - 23 °C
4.2: 81 percent / aq. K3PO4; DMF / PdCl2(dppf)*CHCl3 / diethyl ether; pentane; tetrahydrofuran / 16 h / 23 °C
With
n-butyllithium; potassium tert-butylate; tert.-butyl lithium; tri-n-butyl-tin hydride; 9-methoxy-9-BBN; tricyclohexylphosphine;
palladium diacetate;
In
tetrahydrofuran; diethyl ether; hexane; pentane;
DOI:10.1021/ol0618656
- Guidance literature:
-
Multi-step reaction with 5 steps
1.1: 83 percent / 4 Angstroem molecular sieves; pyridinium chlorochromate; AcOH / CH2Cl2 / 14 h / 0 - 23 °C
2.1: 95 percent / t-BuOK / tetrahydrofuran / 18 h / -55 - 23 °C
3.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C
3.2: 95 percent / tetrahydrofuran; hexane / 1 h / -78 °C
4.1: tricyclohexylphosphine; tributyltin hydride / Pd(OAc)2 / hexane / 15 h / -35 °C
4.2: 29 percent / N-iodosuccinimide / tetrahydrofuran / 2 h / 0 °C
5.1: t-BuLi; 9-methoxy-9-borabicyclo[3.3.1]nonane / diethyl ether; pentane; tetrahydrofuran / -78 - 23 °C
5.2: 81 percent / aq. K3PO4; DMF / PdCl2(dppf)*CHCl3 / diethyl ether; pentane; tetrahydrofuran / 16 h / 23 °C
With
n-butyllithium; 4 A molecular sieve; potassium tert-butylate; tert.-butyl lithium; tri-n-butyl-tin hydride; acetic acid; 9-methoxy-9-BBN; pyridinium chlorochromate; tricyclohexylphosphine;
palladium diacetate;
In
tetrahydrofuran; diethyl ether; hexane; dichloromethane; pentane;
DOI:10.1021/ol0618656
- Guidance literature:
-
Multi-step reaction with 2 steps
1.1: tricyclohexylphosphine; tributyltin hydride / Pd(OAc)2 / hexane / 15 h / -35 °C
1.2: 29 percent / N-iodosuccinimide / tetrahydrofuran / 2 h / 0 °C
2.1: t-BuLi; 9-methoxy-9-borabicyclo[3.3.1]nonane / diethyl ether; pentane; tetrahydrofuran / -78 - 23 °C
2.2: 81 percent / aq. K3PO4; DMF / PdCl2(dppf)*CHCl3 / diethyl ether; pentane; tetrahydrofuran / 16 h / 23 °C
With
tert.-butyl lithium; tri-n-butyl-tin hydride; 9-methoxy-9-BBN; tricyclohexylphosphine;
palladium diacetate;
In
tetrahydrofuran; diethyl ether; hexane; pentane;
DOI:10.1021/ol0618656