Technology Process of 2H-Pyran-2-one,
6-[(1E,3S,4R,6R,7Z,9Z,11E)-6-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-13
-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-4-hydroxy-3-methyl-3-[(triethylsilyl)
oxy]-1,7,9,11-tridecatetraenyl]-5,6-dihydro-, (6R)-
There total 13 articles about 2H-Pyran-2-one,
6-[(1E,3S,4R,6R,7Z,9Z,11E)-6-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-13
-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-4-hydroxy-3-methyl-3-[(triethylsilyl)
oxy]-1,7,9,11-tridecatetraenyl]-5,6-dihydro-, (6R)- 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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872693-82-8
(3'S,4'R,6'R,6R,1'E,7'Z,9'Z,11'E)-6-(6'-tert-butyldimethylsilyloxy-13-tert-butyldiphenylsilyloxy-4'-hydroxy-3'-methyl-3'-triethylsilyloxy-trideca-1',7',9',11'-tetraenyl)-5,6-dihydropyran-2-one
- Guidance literature:
-
With
dichloro bis(acetonitrile) palladium(II);
In
N,N-dimethyl-formamide;
at 40 ℃;
for 24h;
DOI:10.1021/ja0562043
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872693-82-8
(3'S,4'R,6'R,6R,1'E,7'Z,9'Z,11'E)-6-(6'-tert-butyldimethylsilyloxy-13-tert-butyldiphenylsilyloxy-4'-hydroxy-3'-methyl-3'-triethylsilyloxy-trideca-1',7',9',11'-tetraenyl)-5,6-dihydropyran-2-one
- Guidance literature:
-
Multi-step reaction with 11 steps
1: 96 percent / imidazole / dimethylformamide
2: 100 percent / i-Pr2NEt / CH2Cl2
3: 93 percent / Na; NH3 (liq.) / -78 °C
4: 93 percent / MnO2 / CH2Cl2
5: 80 percent / AgF; (R)-p-Tol-BINAP / methanol / -20 °C
6: 76 percent / Et3N / CH2Cl2
7: 94 percent / Grubb's catalyst 1st generation / CH2Cl2
8: 90 percent / Et3N*3HF / tetrahydrofuran
9: 92 percent / Dess-Martin periodinane / CH2Cl2
10: 65 percent / (S)-LLB / tetrahydrofuran / -20 °C
11: 84 percent / PdCl2(CH3CN)2 / dimethylformamide / 24 h / 40 °C
With
1H-imidazole; manganese(IV) oxide; dichloro bis(acetonitrile) palladium(II); (S)-lanthanum-lithium-BINOL; (R)-p-Tol-BINAP; ammonia; sodium; silver fluoride; Dess-Martin periodane; triethylamine tris(hydrogen fluoride); triethylamine; N-ethyl-N,N-diisopropylamine;
Grubbs catalyst first generation;
In
tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
5: Yamamoto allylation / 11: Stille coupling;
DOI:10.1021/ja0562043
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-
872693-82-8
(3'S,4'R,6'R,6R,1'E,7'Z,9'Z,11'E)-6-(6'-tert-butyldimethylsilyloxy-13-tert-butyldiphenylsilyloxy-4'-hydroxy-3'-methyl-3'-triethylsilyloxy-trideca-1',7',9',11'-tetraenyl)-5,6-dihydropyran-2-one
- Guidance literature:
-
Multi-step reaction with 12 steps
1.1: aq. HCl / ethanol / 60 °C
1.2: NaBH4 / methanol
2.1: 96 percent / imidazole / dimethylformamide
3.1: 100 percent / i-Pr2NEt / CH2Cl2
4.1: 93 percent / Na; NH3 (liq.) / -78 °C
5.1: 93 percent / MnO2 / CH2Cl2
6.1: 80 percent / AgF; (R)-p-Tol-BINAP / methanol / -20 °C
7.1: 76 percent / Et3N / CH2Cl2
8.1: 94 percent / Grubb's catalyst 1st generation / CH2Cl2
9.1: 90 percent / Et3N*3HF / tetrahydrofuran
10.1: 92 percent / Dess-Martin periodinane / CH2Cl2
11.1: 65 percent / (S)-LLB / tetrahydrofuran / -20 °C
12.1: 84 percent / PdCl2(CH3CN)2 / dimethylformamide / 24 h / 40 °C
With
1H-imidazole; hydrogenchloride; manganese(IV) oxide; dichloro bis(acetonitrile) palladium(II); (S)-lanthanum-lithium-BINOL; (R)-p-Tol-BINAP; ammonia; sodium; silver fluoride; Dess-Martin periodane; triethylamine tris(hydrogen fluoride); triethylamine; N-ethyl-N,N-diisopropylamine;
Grubbs catalyst first generation;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;
6.1: Yamamoto allylation / 12.1: Stille coupling;
DOI:10.1021/ja0562043