Technology Process of (5S,10R,14S,15R,17S,18S,E)-5-allyl-10-(tert-butyldimethylsilyloxy)-3,3-diethyl-7-hydroxy-20,20-diisopropyl-15-(4-methoxybenzyloxy)-10,14,17,18,21-pentamethyl-4,19-dioxa-3,20-disiladocos-11-en-9-one
There total 18 articles about (5S,10R,14S,15R,17S,18S,E)-5-allyl-10-(tert-butyldimethylsilyloxy)-3,3-diethyl-7-hydroxy-20,20-diisopropyl-15-(4-methoxybenzyloxy)-10,14,17,18,21-pentamethyl-4,19-dioxa-3,20-disiladocos-11-en-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:
-
-
1373432-46-2
(5S,10R,14S,15R,17S,18S,E)-5-allyl-10-(tert-butyldimethylsilyloxy)-3,3-diethyl-7-hydroxy-20,20-diisopropyl-15-(4-methoxybenzyloxy)-10,14,17,18,21-pentamethyl-4,19-dioxa-3,20-disiladocos-11-en-9-one
- Guidance literature:
-
(3R,7S,8R,10S,11S,E)-3-(tert-butyldimethylsilyloxy)-8-(4-methoxybenzyloxy)-3,7,10-trimethyl-11-(triisopropylsilyloxy)dodec-4-en-2-one;
With
lithium diisopropyl amide;
In
tetrahydrofuran;
at -78 ℃;
for 3h;
(S)-3-(triethylsilyloxy)hex-5-enal;
In
tetrahydrofuran;
at -78 ℃;
for 3h;
DOI:10.1021/ol300785c
-
-
1373432-46-2
(5S,10R,14S,15R,17S,18S,E)-5-allyl-10-(tert-butyldimethylsilyloxy)-3,3-diethyl-7-hydroxy-20,20-diisopropyl-15-(4-methoxybenzyloxy)-10,14,17,18,21-pentamethyl-4,19-dioxa-3,20-disiladocos-11-en-9-one
- Guidance literature:
-
Multi-step reaction with 14 steps
1.1: triethylamine / dichloromethane / 0 - 20 °C
2.1: tetra-(n-butyl)ammonium iodide / dimethyl sulfoxide / 48 h / 60 °C
3.1: diisobutylaluminium hydride / hexane; dichloromethane / 3 h / -78 °C
4.1: 1-methyl-pyrrolidin-2-one; titanium tetrachloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 0 °C
4.2: 1 h
5.1: methanol; lithium borohydride / tetrahydrofuran; diethyl ether / 0 - 20 °C
6.1: pyridinium p-toluenesulfonate / dichloromethane / 2 h
6.2: 8 h / -78 - 20 °C
7.1: triethylamine / dichloromethane / 0 - 20 °C
8.1: lithium triethylborohydride / tetrahydrofuran / 20 °C
8.2: 0 °C
9.1: Hoveyda-Grubbs catalyst second generation / dichloromethane / Reflux
10.1: diethyl ether / -78 °C
11.1: 4,4'-di-tert-butylbiphenyl; lithium / tetrahydrofuran / -78 °C
12.1: sulfur trioxide pyridine complex; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 20 °C
13.1: 2,6-dimethylpyridine / dichloromethane / 0 °C
14.1: lithium diisopropyl amide / tetrahydrofuran / 3 h / -78 °C
14.2: 3 h / -78 °C
With
2,6-dimethylpyridine; 1-methyl-pyrrolidin-2-one; methanol; lithium borohydride; Hoveyda-Grubbs catalyst second generation; 4,4'-di-tert-butylbiphenyl; sulfur trioxide pyridine complex; pyridinium p-toluenesulfonate; titanium tetrachloride; tetra-(n-butyl)ammonium iodide; lithium; diisobutylaluminium hydride; lithium triethylborohydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide;
In
tetrahydrofuran; diethyl ether; hexane; dichloromethane; dimethyl sulfoxide;
12.1: Parikh-Doering oxidation / 14.1: Aldol condensation / 14.2: Aldol condensation;
DOI:10.1021/ol300785c
-
-
1373432-46-2
(5S,10R,14S,15R,17S,18S,E)-5-allyl-10-(tert-butyldimethylsilyloxy)-3,3-diethyl-7-hydroxy-20,20-diisopropyl-15-(4-methoxybenzyloxy)-10,14,17,18,21-pentamethyl-4,19-dioxa-3,20-disiladocos-11-en-9-one
- Guidance literature:
-
Multi-step reaction with 13 steps
1.1: tetra-(n-butyl)ammonium iodide / dimethyl sulfoxide / 48 h / 60 °C
2.1: diisobutylaluminium hydride / hexane; dichloromethane / 3 h / -78 °C
3.1: 1-methyl-pyrrolidin-2-one; titanium tetrachloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 0 °C
3.2: 1 h
4.1: methanol; lithium borohydride / tetrahydrofuran; diethyl ether / 0 - 20 °C
5.1: pyridinium p-toluenesulfonate / dichloromethane / 2 h
5.2: 8 h / -78 - 20 °C
6.1: triethylamine / dichloromethane / 0 - 20 °C
7.1: lithium triethylborohydride / tetrahydrofuran / 20 °C
7.2: 0 °C
8.1: Hoveyda-Grubbs catalyst second generation / dichloromethane / Reflux
9.1: diethyl ether / -78 °C
10.1: 4,4'-di-tert-butylbiphenyl; lithium / tetrahydrofuran / -78 °C
11.1: sulfur trioxide pyridine complex; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 20 °C
12.1: 2,6-dimethylpyridine / dichloromethane / 0 °C
13.1: lithium diisopropyl amide / tetrahydrofuran / 3 h / -78 °C
13.2: 3 h / -78 °C
With
2,6-dimethylpyridine; 1-methyl-pyrrolidin-2-one; methanol; lithium borohydride; Hoveyda-Grubbs catalyst second generation; 4,4'-di-tert-butylbiphenyl; sulfur trioxide pyridine complex; pyridinium p-toluenesulfonate; titanium tetrachloride; tetra-(n-butyl)ammonium iodide; lithium; diisobutylaluminium hydride; lithium triethylborohydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide;
In
tetrahydrofuran; diethyl ether; hexane; dichloromethane; dimethyl sulfoxide;
11.1: Parikh-Doering oxidation / 13.1: Aldol condensation / 13.2: Aldol condensation;
DOI:10.1021/ol300785c
