Technology Process of (2E,4E)-5-[(2R,3R,3aR,4R,5R,6aS)-5-Ethyl-4-hydroxy-3-(4-methoxy-benzyloxy)-3a,4-dimethyl-hexahydro-furo[2,3-b]furan-2-yl]-penta-2,4-dienoic acid ethyl ester
There total 10 articles about (2E,4E)-5-[(2R,3R,3aR,4R,5R,6aS)-5-Ethyl-4-hydroxy-3-(4-methoxy-benzyloxy)-3a,4-dimethyl-hexahydro-furo[2,3-b]furan-2-yl]-penta-2,4-dienoic acid ethyl ester which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: KH / tetrahydrofuran / 1 h / 20 °C
1.2: 80 percent / tetrahydrofuran / 20 °C
2.1: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / 20 °C
3.1: 88 percent / HCl / diethyl ether / 1.5 h / 20 °C
4.1: OsO4; NMO
4.2: CSA
5.1: 100 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / 20 °C
6.1: DMSO; oxalyl chloride; triethylamine / CH2Cl2 / -78 - 0 °C
7.1: LDA
With
hydrogenchloride; osmium(VIII) oxide; N-methyl-2-indolinone; oxalyl dichloride; tetrabutyl ammonium fluoride; potassium hydride; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide;
In
tetrahydrofuran; diethyl ether; dichloromethane;
7.1: Swern oxidation / 8.1: Horner-Wadsworth-Emmons olefination;
DOI:10.1021/ja034332q
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: KH / tetrahydrofuran / 1 h / 20 °C
1.2: 80 percent / tetrahydrofuran / 20 °C
2.1: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / 20 °C
3.1: 88 percent / HCl / diethyl ether / 1.5 h / 20 °C
4.1: OsO4; NMO
4.2: CSA
5.1: 100 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / 20 °C
6.1: DMSO; oxalyl chloride; triethylamine / CH2Cl2 / -78 - 0 °C
7.1: LDA
With
hydrogenchloride; osmium(VIII) oxide; N-methyl-2-indolinone; oxalyl dichloride; tetrabutyl ammonium fluoride; potassium hydride; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide;
In
tetrahydrofuran; diethyl ether; dichloromethane;
7.1: Swern oxidation / 8.1: Horner-Wadsworth-Emmons olefination;
DOI:10.1021/ja034332q
- Guidance literature:
-
Multi-step reaction with 6 steps
1.1: 88 percent / HCl / diethyl ether / 1.5 h / 20 °C
2.1: OsO4; NMO
2.2: CSA
3.1: 100 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / 20 °C
4.1: DMSO; oxalyl chloride; triethylamine / CH2Cl2 / -78 - 0 °C
5.1: LDA
With
hydrogenchloride; osmium(VIII) oxide; N-methyl-2-indolinone; oxalyl dichloride; tetrabutyl ammonium fluoride; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide;
In
tetrahydrofuran; diethyl ether; dichloromethane;
5.1: Swern oxidation / 6.1: Horner-Wadsworth-Emmons olefination;
DOI:10.1021/ja034332q