Technology Process of (1S,3S,3aS,4R,4aS,8aR,9aS)-1-Methoxy-3-methyl-4-phenylsulfanylmethyl-dodecahydro-naphtho[2,3-c]furan
There total 21 articles about (1S,3S,3aS,4R,4aS,8aR,9aS)-1-Methoxy-3-methyl-4-phenylsulfanylmethyl-dodecahydro-naphtho[2,3-c]furan 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:
- Guidance literature:
-
With
boron trifluoride diethyl etherate;
In
dichloromethane;
at -20 - 20 ℃;
for 2h;
DOI:10.1021/jo970612a
- Guidance literature:
-
Multi-step reaction with 12 steps
1.1: lithium perchlorate / diethyl ether / 168 h / 20 °C
2.1: 96 percent / H2 / 10 percent Pd/C / ethanol / 12 h / 20 °C / 760 Torr
3.1: 92 percent / LiN(TMS)2 / tetrahydrofuran / -78 - -40 °C
4.1: 83 percent / DBU / toluene / 5 h / 100 °C
5.1: 96 percent / H2 / PtO2 / ethanol / 16 h / 20 °C / 760 Torr
6.1: DIBAL-H / diethyl ether; hexane / 1 h / -78 °C
7.1: 1.50 g / BF3*Et2O / CH2Cl2 / 12 h / -60 °C
8.1: 95 percent / tetrapropylammonium perruthenate(VII); 4-methylmorpholine N-oxide; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C
9.1: NaN(TMS)2 / diethyl ether; toluene / 1 h / 20 °C
9.2: 86 percent / diethyl ether; toluene / 2 h / 20 °C
10.1: BH3*THF / tetrahydrofuran / 3 h / -78 °C
10.2: 73 percent / aq. NaOH; H2O2 / 0.5 h / 0 °C
11.1: triethylamine; 4-(dimethylamino)pyridine / CH2Cl2 / 3 h / 0 °C
12.1: 627 g / t-BuOK / dimethylsulfoxide / 3 h / 20 °C
With
dmap; tetrapropylammonium perruthennate; borane-THF; 4 A molecular sieve; boron trifluoride diethyl etherate; potassium tert-butylate; hydrogen; lithium perchlorate; sodium hexamethyldisilazane; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium hexamethyldisilazane;
platinum(IV) oxide; palladium on activated charcoal;
In
tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; dimethyl sulfoxide; toluene;
1.1: Diels-Alder reaction / 9.2: Wittig reaction;
DOI:10.1016/S0040-4020(02)01358-3
- Guidance literature:
-
Multi-step reaction with 12 steps
1.1: lithium perchlorate / diethyl ether / 168 h / 20 °C
2.1: 96 percent / H2 / 10 percent Pd/C / ethanol / 12 h / 20 °C / 760 Torr
3.1: 92 percent / LiN(TMS)2 / tetrahydrofuran / -78 - -40 °C
4.1: 83 percent / DBU / toluene / 5 h / 100 °C
5.1: 96 percent / H2 / PtO2 / ethanol / 16 h / 20 °C / 760 Torr
6.1: DIBAL-H / diethyl ether; hexane / 1 h / -78 °C
7.1: 1.50 g / BF3*Et2O / CH2Cl2 / 12 h / -60 °C
8.1: 95 percent / tetrapropylammonium perruthenate(VII); 4-methylmorpholine N-oxide; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C
9.1: NaN(TMS)2 / diethyl ether; toluene / 1 h / 20 °C
9.2: 86 percent / diethyl ether; toluene / 2 h / 20 °C
10.1: BH3*THF / tetrahydrofuran / 3 h / -78 °C
10.2: 73 percent / aq. NaOH; H2O2 / 0.5 h / 0 °C
11.1: triethylamine; 4-(dimethylamino)pyridine / CH2Cl2 / 3 h / 0 °C
12.1: 627 g / t-BuOK / dimethylsulfoxide / 3 h / 20 °C
With
dmap; tetrapropylammonium perruthennate; borane-THF; 4 A molecular sieve; boron trifluoride diethyl etherate; potassium tert-butylate; hydrogen; lithium perchlorate; sodium hexamethyldisilazane; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium hexamethyldisilazane;
platinum(IV) oxide; palladium on activated charcoal;
In
tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; dimethyl sulfoxide; toluene;
1.1: Diels-Alder reaction / 9.2: Wittig reaction;
DOI:10.1016/S0040-4020(02)01358-3
