Technology Process of 2,2,2-trichloroethyl ((1R,4R,8R)-9,10,12-trimethoxy-13-(4-methoxybenzyl)-11-methyl-5,14-dioxo-1,3,4,5,7,8-hexahydro-8,1-(epiminomethano)benzo[g][1,5]oxathiecin-4-yl)carbamate
There total 21 articles about 2,2,2-trichloroethyl ((1R,4R,8R)-9,10,12-trimethoxy-13-(4-methoxybenzyl)-11-methyl-5,14-dioxo-1,3,4,5,7,8-hexahydro-8,1-(epiminomethano)benzo[g][1,5]oxathiecin-4-yl)carbamate which
guide to synthetic route it.
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synthetic route:
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1339231-97-8
2,2,2-trichloroethyl ((1R,4R,8R)-9,10,12-trimethoxy-13-(4-methoxybenzyl)-11-methyl-5,14-dioxo-1,3,4,5,7,8-hexahydro-8,1-(epiminomethano)benzo[g][1,5]oxathiecin-4-yl)carbamate
- Guidance literature:
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With
dmap; 2-methyl-6-nitrobenzoic anhydride;
In
dichloromethane;
at 20 ℃;
for 15h;
Inert atmosphere;
DOI:10.1039/c1cc13992d
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1339231-97-8
2,2,2-trichloroethyl ((1R,4R,8R)-9,10,12-trimethoxy-13-(4-methoxybenzyl)-11-methyl-5,14-dioxo-1,3,4,5,7,8-hexahydro-8,1-(epiminomethano)benzo[g][1,5]oxathiecin-4-yl)carbamate
- Guidance literature:
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Multi-step reaction with 12 steps
1: di-isopropyl azodicarboxylate; diphenyl phosphoryl azide; triphenylphosphine / tetrahydrofuran / 6 h / 0 °C / Inert atmosphere
2: water; triphenylphosphine / tetrahydrofuran; water / 3 h / 60 °C / Inert atmosphere
3: methanol / 4 h / Inert atmosphere; Reflux
4: sodium tetrahydroborate / methanol / 2.5 h / 0 - 20 °C / Inert atmosphere
5: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere
6: water; potassium carbonate / methanol / 17 h / 20 °C / Inert atmosphere
7: sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere
8: dichloromethane / 16 h / 20 °C / Inert atmosphere
9: scandium tris(trifluoromethanesulfonate) / dichloromethane / 17 h / Inert atmosphere; Reflux
10: pyridine; hydrogen fluoride; water / acetonitrile / 0 - 20 °C / Inert atmosphere
11: water; potassium carbonate / methanol / 4 h / 20 °C / Inert atmosphere
12: dmap; 2-methyl-6-nitrobenzoic anhydride / dichloromethane / 15 h / 20 °C / Inert atmosphere
With
pyridine; dmap; sodium tetrahydroborate; di-isopropyl azodicarboxylate; diphenyl phosphoryl azide; 2-methyl-6-nitrobenzoic anhydride; hydrogen fluoride; water; sulfur trioxide pyridine complex; potassium carbonate; dimethyl sulfoxide; triethylamine; triphenylphosphine; scandium tris(trifluoromethanesulfonate);
In
tetrahydrofuran; methanol; dichloromethane; water; acetonitrile;
1: Mitsunobu reaction / 7: Parikh-Doering oxidation / 12: Pummerer type cyclisation;
DOI:10.1039/c1cc13992d
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1339231-97-8
2,2,2-trichloroethyl ((1R,4R,8R)-9,10,12-trimethoxy-13-(4-methoxybenzyl)-11-methyl-5,14-dioxo-1,3,4,5,7,8-hexahydro-8,1-(epiminomethano)benzo[g][1,5]oxathiecin-4-yl)carbamate
- Guidance literature:
-
Multi-step reaction with 11 steps
1: water; triphenylphosphine / tetrahydrofuran; water / 3 h / 60 °C / Inert atmosphere
2: methanol / 4 h / Inert atmosphere; Reflux
3: sodium tetrahydroborate / methanol / 2.5 h / 0 - 20 °C / Inert atmosphere
4: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere
5: water; potassium carbonate / methanol / 17 h / 20 °C / Inert atmosphere
6: sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere
7: dichloromethane / 16 h / 20 °C / Inert atmosphere
8: scandium tris(trifluoromethanesulfonate) / dichloromethane / 17 h / Inert atmosphere; Reflux
9: pyridine; hydrogen fluoride; water / acetonitrile / 0 - 20 °C / Inert atmosphere
10: water; potassium carbonate / methanol / 4 h / 20 °C / Inert atmosphere
11: dmap; 2-methyl-6-nitrobenzoic anhydride / dichloromethane / 15 h / 20 °C / Inert atmosphere
With
pyridine; dmap; sodium tetrahydroborate; 2-methyl-6-nitrobenzoic anhydride; hydrogen fluoride; water; sulfur trioxide pyridine complex; potassium carbonate; dimethyl sulfoxide; triethylamine; triphenylphosphine; scandium tris(trifluoromethanesulfonate);
In
tetrahydrofuran; methanol; dichloromethane; water; acetonitrile;
6: Parikh-Doering oxidation / 11: Pummerer type cyclisation;
DOI:10.1039/c1cc13992d