Technology Process of (2S,3R,4E,8E)-2-Azido-3-benzoyloxy-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-4,8-octadecadien
There total 10 articles about (2S,3R,4E,8E)-2-Azido-3-benzoyloxy-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-4,8-octadecadien which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 12 steps
1: 84 percent / tetrahydrofuran / 0.5 h / -20 °C
2: 81 percent / propionsaeure / 3 h / Heating
3: 95 percent / LiAlH4 / diethyl ether
4: 71 percent / pyridine, PBr3 / hexane / Heating from -20 deg C to room temperature.
5: 100 percent / 12 h / 140 °C
6: C6H5Li / 1.) diethyl ether; 2.) toluene, THF, -35 deg C, 20 min.
7: 1.) pyridine, (CF3CO)2O, 2.) NaN3 / 1.) CH2Cl2, -15 deg C, 15 min; 2.) CH2Cl2, DMF, room temperature, 5 h
8: 53 percent / p-toluenesulfonic acid monohydrate / methanol / 12 h / Ambient temperature
9: 96 percent / tetrahydrofuran; pyridine; CHCl3 / 24 h / Ambient temperature
10: 88 percent / toluene; pyridine / 12 h / Ambient temperature
11: 96 percent / BF3-(C2H5)2O / toluene; methanol / 8 h / Ambient temperature
12: 82 percent / BF3-Et2O / CH2Cl2; hexane / 5 h
With
pyridine; lithium aluminium tetrahydride; sodium azide; boron trifluoride diethyl etherate; phosphorus tribromide; toluene-4-sulfonic acid; propionic acid; phenyllithium; trifluoroacetic anhydride;
In
tetrahydrofuran; pyridine; methanol; diethyl ether; hexane; dichloromethane; chloroform; toluene;
- Guidance literature:
-
Multi-step reaction with 11 steps
1: 81 percent / propionsaeure / 3 h / Heating
2: 95 percent / LiAlH4 / diethyl ether
3: 71 percent / pyridine, PBr3 / hexane / Heating from -20 deg C to room temperature.
4: 100 percent / 12 h / 140 °C
5: C6H5Li / 1.) diethyl ether; 2.) toluene, THF, -35 deg C, 20 min.
6: 1.) pyridine, (CF3CO)2O, 2.) NaN3 / 1.) CH2Cl2, -15 deg C, 15 min; 2.) CH2Cl2, DMF, room temperature, 5 h
7: 53 percent / p-toluenesulfonic acid monohydrate / methanol / 12 h / Ambient temperature
8: 96 percent / tetrahydrofuran; pyridine; CHCl3 / 24 h / Ambient temperature
9: 88 percent / toluene; pyridine / 12 h / Ambient temperature
10: 96 percent / BF3-(C2H5)2O / toluene; methanol / 8 h / Ambient temperature
11: 82 percent / BF3-Et2O / CH2Cl2; hexane / 5 h
With
pyridine; lithium aluminium tetrahydride; sodium azide; boron trifluoride diethyl etherate; phosphorus tribromide; toluene-4-sulfonic acid; propionic acid; phenyllithium; trifluoroacetic anhydride;
In
tetrahydrofuran; pyridine; methanol; diethyl ether; hexane; dichloromethane; chloroform; toluene;
- Guidance literature:
-
Multi-step reaction with 10 steps
1: 95 percent / LiAlH4 / diethyl ether
2: 71 percent / pyridine, PBr3 / hexane / Heating from -20 deg C to room temperature.
3: 100 percent / 12 h / 140 °C
4: C6H5Li / 1.) diethyl ether; 2.) toluene, THF, -35 deg C, 20 min.
5: 1.) pyridine, (CF3CO)2O, 2.) NaN3 / 1.) CH2Cl2, -15 deg C, 15 min; 2.) CH2Cl2, DMF, room temperature, 5 h
6: 53 percent / p-toluenesulfonic acid monohydrate / methanol / 12 h / Ambient temperature
7: 96 percent / tetrahydrofuran; pyridine; CHCl3 / 24 h / Ambient temperature
8: 88 percent / toluene; pyridine / 12 h / Ambient temperature
9: 96 percent / BF3-(C2H5)2O / toluene; methanol / 8 h / Ambient temperature
10: 82 percent / BF3-Et2O / CH2Cl2; hexane / 5 h
With
pyridine; lithium aluminium tetrahydride; sodium azide; boron trifluoride diethyl etherate; phosphorus tribromide; toluene-4-sulfonic acid; phenyllithium; trifluoroacetic anhydride;
In
tetrahydrofuran; pyridine; methanol; diethyl ether; hexane; dichloromethane; chloroform; toluene;
