Technology Process of (8R,9S,2Z,6E)-8-fluoro-2,2,11,11,12,12-hexamethyl-3,3-diphenyl-9-styryl-4,10-dioxa-3,11-disilatridec-6-ene
There total 10 articles about (8R,9S,2Z,6E)-8-fluoro-2,2,11,11,12,12-hexamethyl-3,3-diphenyl-9-styryl-4,10-dioxa-3,11-disilatridec-6-ene which
guide to synthetic route it.
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synthetic route:
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1316643-94-3
(8R,9S,2Z,6E)-8-fluoro-2,2,11,11,12,12-hexamethyl-3,3-diphenyl-9-styryl-4,10-dioxa-3,11-disilatridec-6-ene
- Guidance literature:
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O,O-diethyl benzylphosphonate;
With
n-butyllithium;
In
tetrahydrofuran; hexane;
at -78 - -30 ℃;
for 0.833333h;
Inert atmosphere;
(2S,3R,Z)-2-(tert-butyldimethylsilyloxy)-6-(tert-butyldiphenylsilyloxy)-3-fluorohex-4-enal;
In
tetrahydrofuran; hexane;
at 20 ℃;
for 3h;
optical yield given as %de;
stereoselective reaction;
Inert atmosphere;
DOI:10.1021/jo200611w
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1316643-94-3
(8R,9S,2Z,6E)-8-fluoro-2,2,11,11,12,12-hexamethyl-3,3-diphenyl-9-styryl-4,10-dioxa-3,11-disilatridec-6-ene
- Guidance literature:
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Multi-step reaction with 6 steps
1.1: quinoline; Pd-BaSO4; hydrogen / hexane; acetone / 1 h / 20 °C
2.1: 1H-imidazole / dichloromethane / 0.5 h / 20 °C
3.1: 2,6-dimethylpyridine / dichloromethane / 12 h / -40 - 20 °C
4.1: water; 2,3-dicyano-5,6-dichloro-p-benzoquinone / 1,2-dichloro-ethane / 8 h / 50 °C
5.1: sulfur trioxide pyridine complex; N-ethyl-N,N-diisopropylamine / dimethyl sulfoxide / 0.58 h / -30 °C
6.1: n-butyllithium / tetrahydrofuran; hexane / 0.83 h / -78 - -30 °C / Inert atmosphere
6.2: 3 h / 20 °C / Inert atmosphere
With
1H-imidazole; 2,6-dimethylpyridine; quinoline; n-butyllithium; Pd-BaSO4; water; hydrogen; sulfur trioxide pyridine complex; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
In
tetrahydrofuran; hexane; dichloromethane; dimethyl sulfoxide; 1,2-dichloro-ethane; acetone;
6.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1021/jo200611w
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1316643-94-3
(8R,9S,2Z,6E)-8-fluoro-2,2,11,11,12,12-hexamethyl-3,3-diphenyl-9-styryl-4,10-dioxa-3,11-disilatridec-6-ene
- Guidance literature:
-
Multi-step reaction with 10 steps
1.1: titanium(IV) isopropylate; diethyl (2R,3R)-tartrate / dichloromethane / 0.75 h / -20 °C / Molecular sieve
1.2: 18 h / 20 °C / Molecular sieve
2.1: sodium hydride / tetrahydrofuran / 0.33 h / -40 °C / Inert atmosphere
2.2: 2 h / 25 °C / Inert atmosphere
3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.33 h / -5 °C
4.1: triethylamine tris(hydrogen fluoride) / 70 °C / Inert atmosphere
5.1: quinoline; Pd-BaSO4; hydrogen / hexane; acetone / 1 h / 20 °C
6.1: 1H-imidazole / dichloromethane / 0.5 h / 20 °C
7.1: 2,6-dimethylpyridine / dichloromethane / 12 h / -40 - 20 °C
8.1: water; 2,3-dicyano-5,6-dichloro-p-benzoquinone / 1,2-dichloro-ethane / 8 h / 50 °C
9.1: sulfur trioxide pyridine complex; N-ethyl-N,N-diisopropylamine / dimethyl sulfoxide / 0.58 h / -30 °C
10.1: n-butyllithium / tetrahydrofuran; hexane / 0.83 h / -78 - -30 °C / Inert atmosphere
10.2: 3 h / 20 °C / Inert atmosphere
With
1H-imidazole; 2,6-dimethylpyridine; quinoline; titanium(IV) isopropylate; n-butyllithium; diethyl (2R,3R)-tartrate; Pd-BaSO4; tetrabutyl ammonium fluoride; water; hydrogen; sulfur trioxide pyridine complex; sodium hydride; triethylamine tris(hydrogen fluoride); N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
In
tetrahydrofuran; hexane; dichloromethane; dimethyl sulfoxide; 1,2-dichloro-ethane; acetone;
1.1: Sharpless epoxidation / 1.2: Sharpless epoxidation / 10.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1021/jo200611w
