Technology Process of {(2R,4aR,6S,7R,8aS)-6-[(6R,7S)-6-Benzyloxy-7-(3-benzyloxy-propyl)-7-methyl-4,5,6,7-tetrahydro-oxepin-2-ylmethyl]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy}-triethyl-silane
There total 25 articles about {(2R,4aR,6S,7R,8aS)-6-[(6R,7S)-6-Benzyloxy-7-(3-benzyloxy-propyl)-7-methyl-4,5,6,7-tetrahydro-oxepin-2-ylmethyl]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy}-triethyl-silane 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:
-
-
850656-56-3
{(2R,4aR,6S,7R,8aS)-6-[(6R,7S)-6-Benzyloxy-7-(3-benzyloxy-propyl)-7-methyl-4,5,6,7-tetrahydro-oxepin-2-ylmethyl]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy}-triethyl-silane
- Guidance literature:
-
Triethyl-((2R,4aR,7R,8aS)-6-methylene-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy)-silane;
With
9-borabicyclo[3.3.1]nonane dimer;
In
tetrahydrofuran;
at 20 ℃;
for 2h;
Phosphoric acid (6R,7S)-6-benzyloxy-7-(3-benzyloxy-propyl)-7-methyl-4,5,6,7-tetrahydro-oxepin-2-yl ester diphenyl ester;
With
dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate;
In
tetrahydrofuran; N,N-dimethyl-formamide;
at 50 ℃;
for 13.5h;
DOI:10.1021/ja042686r
-
-
850656-56-3
{(2R,4aR,6S,7R,8aS)-6-[(6R,7S)-6-Benzyloxy-7-(3-benzyloxy-propyl)-7-methyl-4,5,6,7-tetrahydro-oxepin-2-ylmethyl]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy}-triethyl-silane
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: 13.39 g / potassium t-butoxide / tetrahydrofuran / 0 - 20 °C
2.1: O3 / CH2Cl2; methanol / 0.58 h / -78 °C
2.2: 90 percent / NaBH4 / CH2Cl2; methanol / -78 - 0 °C
3.1: potassium t-butoxide / tetrahydrofuran / 0 - 20 °C
4.1: aq. HCl / tetrahydrofuran / 8 h / 70 °C
5.1: aq. NaClO2; NaH2PO4; 2-methyl-2-butene / 2-methyl-propan-2-ol / 2 h / 20 °C
6.1: 2,4,6-trichlorobenzoyl chloride; Et3N / tetrahydrofuran / 2 h / 20 °C
6.2: 62 percent / DMAP / toluene; tetrahydrofuran / Heating
7.1: KHMDS; hexamethylphosphoramide / tetrahydrofuran; toluene / 0.75 h / -78 °C
8.1: 9-BBN / tetrahydrofuran / 2 h / 20 °C
8.2: 15.73 g / PdCl2(dppf)*CH2Cl2; aq. Cs2CO3 / dimethylformamide; tetrahydrofuran / 13.5 h / 50 °C
With
hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium chlorite; sodium dihydrogenphosphate; 9-borabicyclo[3.3.1]nonane dimer; 2-methyl-but-2-ene; 2,4,6-trichlorobenzoyl chloride; potassium tert-butylate; potassium hexamethylsilazane; ozone; triethylamine;
In
tetrahydrofuran; methanol; dichloromethane; toluene; tert-butyl alcohol;
8.2: Suzuki-Miyaura cross-coupling;
DOI:10.1021/ja042686r
-
-
850656-56-3
{(2R,4aR,6S,7R,8aS)-6-[(6R,7S)-6-Benzyloxy-7-(3-benzyloxy-propyl)-7-methyl-4,5,6,7-tetrahydro-oxepin-2-ylmethyl]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy}-triethyl-silane
- Guidance literature:
-
Multi-step reaction with 4 steps
1.1: aq. NaClO2; NaH2PO4; 2-methyl-2-butene / 2-methyl-propan-2-ol / 2 h / 20 °C
2.1: 2,4,6-trichlorobenzoyl chloride; Et3N / tetrahydrofuran / 2 h / 20 °C
2.2: 62 percent / DMAP / toluene; tetrahydrofuran / Heating
3.1: KHMDS; hexamethylphosphoramide / tetrahydrofuran; toluene / 0.75 h / -78 °C
4.1: 9-BBN / tetrahydrofuran / 2 h / 20 °C
4.2: 15.73 g / PdCl2(dppf)*CH2Cl2; aq. Cs2CO3 / dimethylformamide; tetrahydrofuran / 13.5 h / 50 °C
With
N,N,N,N,N,N-hexamethylphosphoric triamide; sodium chlorite; sodium dihydrogenphosphate; 9-borabicyclo[3.3.1]nonane dimer; 2-methyl-but-2-ene; 2,4,6-trichlorobenzoyl chloride; potassium hexamethylsilazane; triethylamine;
In
tetrahydrofuran; toluene; tert-butyl alcohol;
4.2: Suzuki-Miyaura cross-coupling;
DOI:10.1021/ja042686r