Technology Process of (2R,5S,6R)-2-[2-(tert-Butyl-dimethyl-silanyloxy)-3,5-dimethoxy-4-methyl-6-((3S,5S)-3,5,7-trimethyl-oct-7-en-1-ynyl)-phenyl]-5-methyl-6-((S)-3-methyl-pent-4-enyl)-[1,3]dioxan-4-one
There total 18 articles about (2R,5S,6R)-2-[2-(tert-Butyl-dimethyl-silanyloxy)-3,5-dimethoxy-4-methyl-6-((3S,5S)-3,5,7-trimethyl-oct-7-en-1-ynyl)-phenyl]-5-methyl-6-((S)-3-methyl-pent-4-enyl)-[1,3]dioxan-4-one which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
isopropoxytrimethylsilane; trimethylsilyl trifluoromethanesulfonate;
In
dichloromethane;
at -20 ℃;
for 12h;
DOI:10.1021/ja060369+
- Guidance literature:
-
Multi-step reaction with 6 steps
1.1: LDA; LiCl / tetrahydrofuran; hexane / 1.33 h / -78 - 20 °C
1.2: 98 percent / tetrahydrofuran; hexane / 14 h / 20 °C
2.1: 97 percent / LDA; BH3*NH3 / tetrahydrofuran; hexane / 3 h / 20 °C
3.1: 89 percent / Et3N; SO3*Py; DMSO / CH2Cl2 / 1 h / 0 °C
4.1: t-BuOK / tetrahydrofuran / 0.25 h / -78 °C
4.2: 77 percent / tetrahydrofuran / 1 h / -78 °C
5.1: 85 percent / PdCl2(PPh3)2; CuI; diisopropylamine / 6.5 h / 60 °C
6.1: 26 percent / isopropyloxytrimethylsilane; TMSOTf / CH2Cl2 / 12 h / -20 °C
With
bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; borane-ammonia complex; pyridine-SO3 complex; isopropoxytrimethylsilane; trimethylsilyl trifluoromethanesulfonate; potassium tert-butylate; dimethyl sulfoxide; triethylamine; diisopropylamine; lithium chloride; lithium diisopropyl amide;
In
tetrahydrofuran; hexane; dichloromethane;
1.2: Myers alkylation / 3.1: Parikh-Doering oxidation / 5.1: Sonogashira reaction / 6.1: Kurihara condensation;
DOI:10.1021/ja060369+
- Guidance literature:
-
Multi-step reaction with 2 steps
1: 85 percent / PdCl2(PPh3)2; CuI; diisopropylamine / 6.5 h / 60 °C
2: 26 percent / isopropyloxytrimethylsilane; TMSOTf / CH2Cl2 / 12 h / -20 °C
With
bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; isopropoxytrimethylsilane; trimethylsilyl trifluoromethanesulfonate; diisopropylamine;
In
dichloromethane;
1: Sonogashira reaction / 2: Kurihara condensation;
DOI:10.1021/ja060369+
