Technology Process of (1S,2S,3R,4R)-3-(tert-butyldiphenylsilyloxy)-4-((tert-butyldiphenylsilyloxy)methyl)-2-fluorocyclopentanol
There total 14 articles about (1S,2S,3R,4R)-3-(tert-butyldiphenylsilyloxy)-4-((tert-butyldiphenylsilyloxy)methyl)-2-fluorocyclopentanol which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
tert-butyl(((1R,2R,3S,4S)-2-(tert-butyldiphenylsilyloxy)-3-fluoro-4-(4-methoxybenzyloxy)cyclopentyl)methoxy)diphenylsilane;
With
2,3-dicyano-5,6-dichloro-p-benzoquinone;
In
dichloromethane;
at 20 ℃;
for 2h;
With
water; sodium carbonate;
In
dichloromethane;
at 20 ℃;
DOI:10.1016/j.tet.2012.03.023
- Guidance literature:
-
Multi-step reaction with 10 steps
1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C
1.2: 3 h / 0 - 20 °C
2.1: hydrogenchloride / methanol / 25 °C
3.1: 1H-imidazole; dmap / dichloromethane / 2 h / 0 - 20 °C
4.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 24 h / -40 - 60 °C
5.1: lithium hydroxide / methanol / 2 h / 25 °C
6.1: pyridine; diethylamino-sulfur trifluoride / dichloromethane / 12 h / 20 °C / Inert atmosphere
7.1: sodium periodate; osmium(VIII) oxide; water; 4-methylmorpholine N-oxide / methanol / 2 h / 0 °C
8.1: methanol; sodium tetrahydroborate / 1 h / 0 °C
9.1: 1H-imidazole; dmap / dichloromethane / 2 h / 0 - 20 °C
10.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 2 h / 20 °C
10.2: 20 °C
With
pyridine; 1H-imidazole; hydrogenchloride; methanol; dmap; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; diethylamino-sulfur trifluoride; di-isopropyl azodicarboxylate; water; sodium hydride; 4-methylmorpholine N-oxide; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hydroxide;
In
tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; mineral oil;
4.1: Mitsunobu reaction;
DOI:10.1016/j.tet.2012.03.023
- Guidance literature:
-
Multi-step reaction with 9 steps
1.1: hydrogenchloride / methanol / 25 °C
2.1: 1H-imidazole; dmap / dichloromethane / 2 h / 0 - 20 °C
3.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 24 h / -40 - 60 °C
4.1: lithium hydroxide / methanol / 2 h / 25 °C
5.1: pyridine; diethylamino-sulfur trifluoride / dichloromethane / 12 h / 20 °C / Inert atmosphere
6.1: sodium periodate; osmium(VIII) oxide; water; 4-methylmorpholine N-oxide / methanol / 2 h / 0 °C
7.1: methanol; sodium tetrahydroborate / 1 h / 0 °C
8.1: 1H-imidazole; dmap / dichloromethane / 2 h / 0 - 20 °C
9.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 2 h / 20 °C
9.2: 20 °C
With
pyridine; 1H-imidazole; hydrogenchloride; methanol; dmap; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; diethylamino-sulfur trifluoride; di-isopropyl azodicarboxylate; water; 4-methylmorpholine N-oxide; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hydroxide;
In
tetrahydrofuran; methanol; dichloromethane;
3.1: Mitsunobu reaction;
DOI:10.1016/j.tet.2012.03.023
