Technology Process of [4S,6R,11R,4'S,1R,2S,1'E]-2,2-dimethyl-11-[2,4-dimethyl-5-[(tert-butyldimethylsilyl)oxy]-1-pentenyl]-4-[1-methyl-2-[(tert-butyldimethylsilyl)oxy]-3-phenylmethoxy-propyl]-1,3,7-trioxaspiroundecan-9-one
There total 18 articles about [4S,6R,11R,4'S,1R,2S,1'E]-2,2-dimethyl-11-[2,4-dimethyl-5-[(tert-butyldimethylsilyl)oxy]-1-pentenyl]-4-[1-methyl-2-[(tert-butyldimethylsilyl)oxy]-3-phenylmethoxy-propyl]-1,3,7-trioxaspiroundecan-9-one which
guide to synthetic route it.
The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:
synthetic route:
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![[4S,6R,11R,4'S,1R,2S,1'E]-2,2-dimethyl-11-[2,4-dimethyl-5-[(tert-butyldimethylsilyl)oxy]-1-pentenyl]-4-[1-methyl-2-[(tert-butyldimethylsilyl)oxy]-3-phenylmethoxy-propyl]-1,3,7-trioxaspiroundecan-9-one](/Databaselist/images/loading.webp)
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197246-57-4
[4S,6R,11R,4'S,1R,2S,1'E]-2,2-dimethyl-11-[2,4-dimethyl-5-[(tert-butyldimethylsilyl)oxy]-1-pentenyl]-4-[1-methyl-2-[(tert-butyldimethylsilyl)oxy]-3-phenylmethoxy-propyl]-1,3,7-trioxaspiroundecan-9-one
- Guidance literature:
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(4R)-5-<(tert-Butyldimethylsilyl)oxy>-4-methyl-1-pentyne; trimethylaluminum;
With
zirconocene dichloride;
In
1,2-dichloro-ethane; toluene;
at 20 ℃;
for 3h;
With
Li2(CN)Cu(CCC4H9)2;
In
tetrahydrofuran; diethyl ether; hexane;
at -30 - -23 ℃;
for 0.25h;
(4S,6R,1'R,2'S)-2,2-dimethyl-4-[1-methyl-2-[(tert-butyldimethylsilyl)-oxy]-3-phenylmethoxy-propyl]-1,3,7-trioxa-spiroundec-10-en-9-one;
In
tetrahydrofuran; diethyl ether; hexane;
at -23 ℃;
for 1h;
DOI:10.1016/S0040-4020(97)00865-X
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197246-57-4
[4S,6R,11R,4'S,1R,2S,1'E]-2,2-dimethyl-11-[2,4-dimethyl-5-[(tert-butyldimethylsilyl)oxy]-1-pentenyl]-4-[1-methyl-2-[(tert-butyldimethylsilyl)oxy]-3-phenylmethoxy-propyl]-1,3,7-trioxaspiroundecan-9-one
- Guidance literature:
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Multi-step reaction with 9 steps
1.1: 29.9 g / imidazole; DMAP / dimethylformamide / 12 h
2.1: 23 percent / N-methylmorpholine-N-oxide / osmium tetroxide / acetone; H2O; benzene / 16 h / 20 °C
3.1: pyridine; DMAP / 1 h / 0 °C
4.1: pyridine; DMAP / 12 h / 20 °C
5.1: 0.321 g / sodium methoxide / methanol / 0.5 h / 0 °C
6.1: n-butyl lithium / tetrahydrofuran; hexane / 0.33 h / -78 - -30 °C
6.2: borontrifluoride etherate / tetrahydrofuran; hexane / 0.5 h / -78 °C
7.1: 0.501 g / pyridinium p-toluenesulfonate / tetrahydrofuran; H2O / 3 h
8.1: MCPBA / CH2Cl2 / 1 h / 0 °C
8.2: 77 percent / conc. HCl / CH2Cl2 / 2 h / 0 °C
9.1: zirconocene dichloride / 1,2-dichloro-ethane; toluene / 3 h / 20 °C
9.2: Li2(CN)Cu(CCC4H9)2 / diethyl ether; tetrahydrofuran; hexane / 0.25 h / -30 - -23 °C
9.3: 90 percent / diethyl ether; tetrahydrofuran; hexane / 1 h / -23 °C
With
pyridine; 1H-imidazole; dmap; n-butyllithium; zirconocene dichloride; sodium methylate; pyridinium p-toluenesulfonate; 4-methylmorpholine N-oxide; 3-chloro-benzenecarboperoxoic acid;
osmium(VIII) oxide;
In
tetrahydrofuran; methanol; hexane; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetone; toluene; benzene;
1.1: silylation / 2.1: dihydroxylation / 3.1: Esterification / 4.1: Esterification / 5.1: Cyclization / 6.1: Metallation / 6.2: Addition / 7.1: Hydrolysis / 8.1: Oxidation / 8.2: spiroketalization / 9.1: Negishi carboalumination / 9.2: transmetalation / 9.3: Addition;
DOI:10.1016/S0040-4020(97)00865-X
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197246-57-4
[4S,6R,11R,4'S,1R,2S,1'E]-2,2-dimethyl-11-[2,4-dimethyl-5-[(tert-butyldimethylsilyl)oxy]-1-pentenyl]-4-[1-methyl-2-[(tert-butyldimethylsilyl)oxy]-3-phenylmethoxy-propyl]-1,3,7-trioxaspiroundecan-9-one
- Guidance literature:
-
Multi-step reaction with 9 steps
1.1: 29.9 g / imidazole; DMAP / dimethylformamide / 12 h
2.1: 23 percent / N-methylmorpholine-N-oxide / osmium tetroxide / acetone; H2O; benzene / 16 h / 20 °C
3.1: pyridine; DMAP / 1 h / 0 °C
4.1: pyridine; DMAP / 12 h / 20 °C
5.1: 0.321 g / sodium methoxide / methanol / 0.5 h / 0 °C
6.1: n-butyl lithium / tetrahydrofuran; hexane / 0.33 h / -78 - -30 °C
6.2: borontrifluoride etherate / tetrahydrofuran; hexane / 0.5 h / -78 °C
7.1: 0.501 g / pyridinium p-toluenesulfonate / tetrahydrofuran; H2O / 3 h
8.1: MCPBA / CH2Cl2 / 1 h / 0 °C
8.2: 77 percent / conc. HCl / CH2Cl2 / 2 h / 0 °C
9.1: zirconocene dichloride / 1,2-dichloro-ethane; toluene / 3 h / 20 °C
9.2: Li2(CN)Cu(CCC4H9)2 / diethyl ether; tetrahydrofuran; hexane / 0.25 h / -30 - -23 °C
9.3: 90 percent / diethyl ether; tetrahydrofuran; hexane / 1 h / -23 °C
With
pyridine; 1H-imidazole; dmap; n-butyllithium; zirconocene dichloride; sodium methylate; pyridinium p-toluenesulfonate; 4-methylmorpholine N-oxide; 3-chloro-benzenecarboperoxoic acid;
osmium(VIII) oxide;
In
tetrahydrofuran; methanol; hexane; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetone; toluene; benzene;
1.1: silylation / 2.1: dihydroxylation / 3.1: Esterification / 4.1: Esterification / 5.1: Cyclization / 6.1: Metallation / 6.2: Addition / 7.1: Hydrolysis / 8.1: Oxidation / 8.2: spiroketalization / 9.1: Negishi carboalumination / 9.2: transmetalation / 9.3: Addition;
DOI:10.1016/S0040-4020(97)00865-X
