Technology Process of (4aS,6R,7S,9aR)-6-(3-Benzyloxy-propyl)-3,4,4a,6,7,9a-hexahydro-2H-1,5-dioxa-benzocyclohepten-7-ol
There total 10 articles about (4aS,6R,7S,9aR)-6-(3-Benzyloxy-propyl)-3,4,4a,6,7,9a-hexahydro-2H-1,5-dioxa-benzocyclohepten-7-ol which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
sodium tetrahydroborate; cerium(III) chloride;
In
methanol;
at 25 ℃;
for 0.5h;
DOI:10.1055/s-2001-13387
- Guidance literature:
-
Multi-step reaction with 9 steps
1.1: BuLi / tetrahydrofuran / 1 h / -78 °C
1.2: 89 percent / BuLi / tetrahydrofuran / 4 h / -78 - 0 °C
2.1: H2; quinoline / Lindlar catalyst / ethanol / 28 h / 20 °C
3.1: (COCl)2; Et3N; DMSO / CH2Cl2 / 0.75 h / -78 - 20 °C
4.1: LDA / tetrahydrofuran / 0.5 h / -78 °C
4.2: 85 percent / tetrahydrofuran / 1.5 h / -78 °C
5.1: 100 percent / TBAF / tetrahydrofuran / 5 h / 20 °C
6.1: TFA / H2O; tetrahydrofuran / 2 h / 20 °C
7.1: Et3SiH; TMSOTf / CH2Cl2 / 1 h / 0 °C
8.1: 47 percent / CH2Cl2 / 3 h / 20 °C
9.1: 84 percent / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 25 °C
With
quinoline; triethylsilane; sodium tetrahydroborate; n-butyllithium; cerium(III) chloride; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; hydrogen; dimethyl sulfoxide; triethylamine; trifluoroacetic acid; lithium diisopropyl amide;
Lindlar's catalyst;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; water;
3.1: Swern oxidation / 8.1: Dess-Martin periodinane / 9.1: Luche reduction;
DOI:10.1055/s-2001-13387
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: H2; quinoline / Lindlar catalyst / ethanol / 28 h / 20 °C
2.1: (COCl)2; Et3N; DMSO / CH2Cl2 / 0.75 h / -78 - 20 °C
3.1: LDA / tetrahydrofuran / 0.5 h / -78 °C
3.2: 85 percent / tetrahydrofuran / 1.5 h / -78 °C
4.1: 100 percent / TBAF / tetrahydrofuran / 5 h / 20 °C
5.1: TFA / H2O; tetrahydrofuran / 2 h / 20 °C
6.1: Et3SiH; TMSOTf / CH2Cl2 / 1 h / 0 °C
7.1: 47 percent / CH2Cl2 / 3 h / 20 °C
8.1: 84 percent / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 25 °C
With
quinoline; triethylsilane; sodium tetrahydroborate; cerium(III) chloride; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; hydrogen; dimethyl sulfoxide; triethylamine; trifluoroacetic acid; lithium diisopropyl amide;
Lindlar's catalyst;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; water;
2.1: Swern oxidation / 7.1: Dess-Martin periodinane / 8.1: Luche reduction;
DOI:10.1055/s-2001-13387
