Technology Process of Oxonin,
2-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-2,3,4,5,8,9-hexahydro-7-
methyl-9-[(1E)-2-methyl-1,3-butadien-1-yl]-3-(triphenylmethoxy)-,
(2R,3R,6E,9R)-
There total 12 articles about Oxonin,
2-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-2,3,4,5,8,9-hexahydro-7-
methyl-9-[(1E)-2-methyl-1,3-butadien-1-yl]-3-(triphenylmethoxy)-,
(2R,3R,6E,9R)- 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:
-
Methyltriphenylphosphonium bromide;
With
sodium hexamethyldisilazane;
In
tetrahydrofuran;
at -78 - 0 ℃;
3-[9-(tert-butyl-diphenyl-silanyloxymethyl)-4-methyl-8-trityloxy-2,3,6,7,8,9-hexahydro-oxonin-2-yl]-2-methyl-propenal;
In
tetrahydrofuran;
at -78 - 20 ℃;
for 2h;
DOI:10.1021/ja065782w
- Guidance literature:
-
Multi-step reaction with 10 steps
1.1: 92 percent / imidazole / CH2Cl2 / 0.5 h / 0 °C
2.1: 93 percent / DMAP; pyridine / 6 h / 100 °C
3.1: 88 percent / DDQ; aq. phosphate buffer / CH2Cl2 / 1 h / 0 °C / pH 8.0
4.1: NaH / tetrahydrofuran / 0.17 h / 0 °C
4.2: 88 percent / tetrahydrofuran / 3 h / 20 °C
5.1: SeO2 / pyridine; ethanol / 6 h / 80 °C
5.2: 924.0 mg / NaBH4 / ethanol / 0.5 h / 0 °C
6.1: 93 percent / CCl4; PPh3; pyridine / 2 h / Heating
7.1: 92 percent / LiHMDS / tetrahydrofuran / 1 h / 45 °C
8.1: n-BuLi; DIBAL-H / tetrahydrofuran; hexane; toluene / 0.5 h / 0 - 20 °C
9.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 - 0 °C
9.2: tetrahydrofuran; hexane / 1 h / -78 °C
9.3: 93.6 mg / aq. oxalic acid / tetrahydrofuran; hexane; diethyl ether / 1 h / 20 °C
10.1: NaHMDS / tetrahydrofuran / -78 - 0 °C
10.2: 97 percent / tetrahydrofuran / 2 h / -78 - 20 °C
With
pyridine; 1H-imidazole; tetrachloromethane; dmap; n-butyllithium; selenium(IV) oxide; phosphate buffer; sodium hexamethyldisilazane; sodium hydride; diisobutylaluminium hydride; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hexamethyldisilazane;
In
tetrahydrofuran; pyridine; ethanol; hexane; dichloromethane; toluene;
9.2: Corey olefination / 10.2: Wittig methylenation;
DOI:10.1021/ja065782w
- Guidance literature:
-
Multi-step reaction with 11 steps
1.1: 89 percent / NaBH4 / tetrahydrofuran; H2O / 2 h / 20 °C
2.1: 92 percent / imidazole / CH2Cl2 / 0.5 h / 0 °C
3.1: 93 percent / DMAP; pyridine / 6 h / 100 °C
4.1: 88 percent / DDQ; aq. phosphate buffer / CH2Cl2 / 1 h / 0 °C / pH 8.0
5.1: NaH / tetrahydrofuran / 0.17 h / 0 °C
5.2: 88 percent / tetrahydrofuran / 3 h / 20 °C
6.1: SeO2 / pyridine; ethanol / 6 h / 80 °C
6.2: 924.0 mg / NaBH4 / ethanol / 0.5 h / 0 °C
7.1: 93 percent / CCl4; PPh3; pyridine / 2 h / Heating
8.1: 92 percent / LiHMDS / tetrahydrofuran / 1 h / 45 °C
9.1: n-BuLi; DIBAL-H / tetrahydrofuran; hexane; toluene / 0.5 h / 0 - 20 °C
10.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 - 0 °C
10.2: tetrahydrofuran; hexane / 1 h / -78 °C
10.3: 93.6 mg / aq. oxalic acid / tetrahydrofuran; hexane; diethyl ether / 1 h / 20 °C
11.1: NaHMDS / tetrahydrofuran / -78 - 0 °C
11.2: 97 percent / tetrahydrofuran / 2 h / -78 - 20 °C
With
pyridine; 1H-imidazole; tetrachloromethane; dmap; sodium tetrahydroborate; n-butyllithium; selenium(IV) oxide; phosphate buffer; sodium hexamethyldisilazane; sodium hydride; diisobutylaluminium hydride; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hexamethyldisilazane;
In
tetrahydrofuran; pyridine; ethanol; hexane; dichloromethane; water; toluene;
10.2: Corey olefination / 11.2: Wittig methylenation;
DOI:10.1021/ja065782w
![3-[9-(<i>tert</i>-butyl-diphenyl-silanyloxymethyl)-4-methyl-8-trityloxy-2,3,6,7,8,9-hexahydro-oxonin-2-yl]-2-methyl-propenal](/Databaselist/images/loading.webp)
