Technology Process of (S,Z)-5-((2S,5R,6R)-5-(tert-butyldimethylsilyloxy)-6-methoxy-2-methyltetrahydro-2H-pyran-2-yl)-2,2,3,3,12,12-hexamethyl-11,11-diphenyl-4,10-dioxa-3,11-disilatridec-6-ene
There total 8 articles about (S,Z)-5-((2S,5R,6R)-5-(tert-butyldimethylsilyloxy)-6-methoxy-2-methyltetrahydro-2H-pyran-2-yl)-2,2,3,3,12,12-hexamethyl-11,11-diphenyl-4,10-dioxa-3,11-disilatridec-6-ene which
guide to synthetic route it.
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synthetic route:
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1352577-47-9
(S)-5-((2S,5R,6R)-5-(tert-butyldimethylsilyloxy)-6-methoxy-2-methyltetrahydro-2H-pyran-2-yl)-2,2,3,3,12,12-hexamethyl-11,11-diphenyl-4,10-dioxa-3,11-disilatridec-6-yne
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1352577-32-2
(S,Z)-5-((2S,5R,6R)-5-(tert-butyldimethylsilyloxy)-6-methoxy-2-methyltetrahydro-2H-pyran-2-yl)-2,2,3,3,12,12-hexamethyl-11,11-diphenyl-4,10-dioxa-3,11-disilatridec-6-ene
- Guidance literature:
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With
quinoline; Lindlar's catalyst; hydrogen;
In
diethyl ether;
at 23 ℃;
for 18h;
stereoselective reaction;
DOI:10.1016/j.tet.2011.09.079
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1352577-32-2
(S,Z)-5-((2S,5R,6R)-5-(tert-butyldimethylsilyloxy)-6-methoxy-2-methyltetrahydro-2H-pyran-2-yl)-2,2,3,3,12,12-hexamethyl-11,11-diphenyl-4,10-dioxa-3,11-disilatridec-6-ene
- Guidance literature:
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Multi-step reaction with 8 steps
1.1: potassium hexamethylsilazane / tetrahydrofuran / 0.42 h / -78 °C / Inert atmosphere
1.2: 19 h / -78 - 23 °C / Inert atmosphere
2.1: Grubbs catalyst first generation / toluene / 2.75 h / 23 °C / Inert atmosphere
2.2: 0.17 h / 23 °C / Inert atmosphere
2.3: 14.5 h / 108 °C / Inert atmosphere
3.1: 3-chloro-benzenecarboperoxoic acid / 3 h / 0 °C / Inert atmosphere
4.1: 1H-imidazole / N,N-dimethyl-formamide / 3 h / 60 °C / Inert atmosphere
5.1: diisobutylaluminium hydride / diethyl ether; hexane / 0.58 h / -78 °C / Inert atmosphere
5.2: 15 h / -78 - 23 °C / Inert atmosphere
6.1: (1S,2R)-(+)-N-methylephedrine; zinc trifluoromethanesulfonate; triethylamine / toluene / 0.25 h / 23 °C / Inert atmosphere
6.2: 18 h / 23 °C / Inert atmosphere
6.3: 0.08 h / 23 °C / Inert atmosphere
7.1: 2,6-dimethylpyridine / dichloromethane / 1.17 h / -78 - 0 °C / Inert atmosphere
8.1: quinoline; Lindlar's catalyst; hydrogen / diethyl ether / 18 h / 23 °C
With
1H-imidazole; 2,6-dimethylpyridine; Grubbs catalyst first generation; quinoline; Lindlar's catalyst; (1S,2R)-(+)-N-methylephedrine; hydrogen; potassium hexamethylsilazane; zinc trifluoromethanesulfonate; diisobutylaluminium hydride; triethylamine; 3-chloro-benzenecarboperoxoic acid;
In
tetrahydrofuran; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1016/j.tet.2011.09.079
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1352577-32-2
(S,Z)-5-((2S,5R,6R)-5-(tert-butyldimethylsilyloxy)-6-methoxy-2-methyltetrahydro-2H-pyran-2-yl)-2,2,3,3,12,12-hexamethyl-11,11-diphenyl-4,10-dioxa-3,11-disilatridec-6-ene
- Guidance literature:
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Multi-step reaction with 6 steps
1.1: 3-chloro-benzenecarboperoxoic acid / 3 h / 0 °C / Inert atmosphere
2.1: 1H-imidazole / N,N-dimethyl-formamide / 3 h / 60 °C / Inert atmosphere
3.1: diisobutylaluminium hydride / diethyl ether; hexane / 0.58 h / -78 °C / Inert atmosphere
3.2: 15 h / -78 - 23 °C / Inert atmosphere
4.1: (1S,2R)-(+)-N-methylephedrine; zinc trifluoromethanesulfonate; triethylamine / toluene / 0.25 h / 23 °C / Inert atmosphere
4.2: 18 h / 23 °C / Inert atmosphere
4.3: 0.08 h / 23 °C / Inert atmosphere
5.1: 2,6-dimethylpyridine / dichloromethane / 1.17 h / -78 - 0 °C / Inert atmosphere
6.1: quinoline; Lindlar's catalyst; hydrogen / diethyl ether / 18 h / 23 °C
With
1H-imidazole; 2,6-dimethylpyridine; quinoline; Lindlar's catalyst; (1S,2R)-(+)-N-methylephedrine; hydrogen; zinc trifluoromethanesulfonate; diisobutylaluminium hydride; triethylamine; 3-chloro-benzenecarboperoxoic acid;
In
diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1016/j.tet.2011.09.079
