Technology Process of tert-butyl(((S)-1-((3aS,4S,6S,7aS)-4-((4R,5S)-5-((4-methoxybenzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl)-4-(trimethylsilyl)pent-4-en-1-yl)oxy)dimethylsilane
There total 20 articles about tert-butyl(((S)-1-((3aS,4S,6S,7aS)-4-((4R,5S)-5-((4-methoxybenzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl)-4-(trimethylsilyl)pent-4-en-1-yl)oxy)dimethylsilane which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 12 steps
1.1: dichloromethane / 1 h / 20 °C
2.1: diisobutylaluminium hydride / toluene; hexane / -78 - 0 °C
3.1: potassium tert-butylate / tetrahydrofuran / 3 h / 0 - 20 °C
4.1: AD-mix-β; 1,4-bis(9-O-dihydroquinidine)phthalazine; potassium osmate(VI) dihydrate; methanesulfonamide / tert-butyl alcohol / pH 7
5.1: toluene-4-sulfonic acid / acetone / 4 h / 0 - 20 °C
6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 0 - 20 °C
7.1: dimethyl sulfoxide; oxalyl dichloride / dichloromethane / 0.33 h / -60 °C
7.2: -60 - 20 °C
8.1: potassium tert-butylate / tetrahydrofuran / -10 - 20 °C
8.2: -10 - 20 °C
9.1: hydroquinidein 1,4-phthalazinediyl diether; potassium hexacyanoferrate(III); potassium carbonate; potassium osmate(VI) dihydrate; methanesulfonamide / tert-butyl alcohol / pH 7
10.1: pyridinium p-toluenesulfonate; Trimethyl orthoacetate / dichloromethane / 2 h / 20 °C
10.2: 5 h / 20 °C
10.3: 20 °C
11.1: n-butyllithium / tetrahydrofuran; hexane / 0.33 h / -78 °C
11.2: 1 h / -78 °C
12.1: 2,6-dimethylpyridine / dichloromethane / -78 - 20 °C
With
2,6-dimethylpyridine; Trimethyl orthoacetate; potassium osmate(VI) dihydrate; n-butyllithium; oxalyl dichloride; methanesulfonamide; AD-mix-β; potassium tert-butylate; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; hydroquinidein 1,4-phthalazinediyl diether; 1,4-bis(9-O-dihydroquinidine)phthalazine; potassium hexacyanoferrate(III);
In
tetrahydrofuran; hexane; dichloromethane; acetone; toluene; tert-butyl alcohol;
4.1: |Sharpless Dihydroxylation / 7.1: |Swern Oxidation / 7.2: |Swern Oxidation / 9.1: |Sharpless Dihydroxylation;
DOI:10.1016/j.tet.2013.05.067
- Guidance literature:
-
Multi-step reaction with 5 steps
1.1: potassium tert-butylate / tetrahydrofuran / -10 - 20 °C
1.2: -10 - 20 °C
2.1: hydroquinidein 1,4-phthalazinediyl diether; potassium hexacyanoferrate(III); potassium carbonate; potassium osmate(VI) dihydrate; methanesulfonamide / tert-butyl alcohol / pH 7
3.1: pyridinium p-toluenesulfonate; Trimethyl orthoacetate / dichloromethane / 2 h / 20 °C
3.2: 5 h / 20 °C
3.3: 20 °C
4.1: n-butyllithium / tetrahydrofuran; hexane / 0.33 h / -78 °C
4.2: 1 h / -78 °C
5.1: 2,6-dimethylpyridine / dichloromethane / -78 - 20 °C
With
2,6-dimethylpyridine; Trimethyl orthoacetate; potassium osmate(VI) dihydrate; n-butyllithium; methanesulfonamide; potassium tert-butylate; pyridinium p-toluenesulfonate; potassium carbonate; hydroquinidein 1,4-phthalazinediyl diether; potassium hexacyanoferrate(III);
In
tetrahydrofuran; hexane; dichloromethane; tert-butyl alcohol;
2.1: |Sharpless Dihydroxylation;
DOI:10.1016/j.tet.2013.05.067
