Technology Process of {3-[(3S,6S,8R,12S,14S)-12-(4-Benzyloxy-benzyl)-6-(1H-indol-3-ylmethyl)-2,5-dioxo-10-oxa-1,4,7-triaza-tricyclo[6.4.2.04,14]tetradec-3-yl]-propyl}-carbamic acid benzyl ester
There total 26 articles about {3-[(3S,6S,8R,12S,14S)-12-(4-Benzyloxy-benzyl)-6-(1H-indol-3-ylmethyl)-2,5-dioxo-10-oxa-1,4,7-triaza-tricyclo[6.4.2.04,14]tetradec-3-yl]-propyl}-carbamic acid benzyl ester 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
diphenylphosphoranyl azide; sodium hydrogencarbonate;
In
N,N-dimethyl-formamide;
at 0 ℃;
for 15h;
DOI:10.1021/jo961114p
- Guidance literature:
-
Multi-step reaction with 13 steps
1: 72 percent / dioxane / 9 h / Heating
2: 80 percent / triethylamine / CH2Cl2 / 1.17 h
3: 99 percent / collidine / CH2Cl2 / 1.25 h
4: 79 percent / triethylamine / acetonitrile / 10 h / Heating
5: 66 percent / PCl5 / tetrahydrofuran / 1.75 h / 0 °C
6: 82 percent / Bu4NF / tetrahydrofuran / 0.5 h
7: 94 percent / triethylamine / CH2Cl2 / 1.5 h / Ambient temperature
8: NaH / dimethylsulfoxide / 2 h
9: NaBH4 / methanol
10: NaI / acetone / Heating
11: 1.) NaHCO3 / 1.) H2O, 2.) CH3CN, room temp., 41 h
12: 100 percent / aq. LiOH / tetrahydrofuran / 3 h
13: 19 percent / diphenylphosphoryl azide, NaHCO3 / dimethylformamide / 15 h / 0 °C
With
2,3,5-trimethyl-pyridine; lithium hydroxide; sodium tetrahydroborate; phosphorus pentachloride; diphenylphosphoranyl azide; tetrabutyl ammonium fluoride; sodium hydride; sodium hydrogencarbonate; triethylamine; sodium iodide;
In
tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; acetonitrile;
DOI:10.1021/jo961114p
- Guidance literature:
-
Multi-step reaction with 12 steps
1: 80 percent / triethylamine / CH2Cl2 / 1.17 h
2: 99 percent / collidine / CH2Cl2 / 1.25 h
3: 79 percent / triethylamine / acetonitrile / 10 h / Heating
4: 66 percent / PCl5 / tetrahydrofuran / 1.75 h / 0 °C
5: 82 percent / Bu4NF / tetrahydrofuran / 0.5 h
6: 94 percent / triethylamine / CH2Cl2 / 1.5 h / Ambient temperature
7: NaH / dimethylsulfoxide / 2 h
8: NaBH4 / methanol
9: NaI / acetone / Heating
10: 1.) NaHCO3 / 1.) H2O, 2.) CH3CN, room temp., 41 h
11: 100 percent / aq. LiOH / tetrahydrofuran / 3 h
12: 19 percent / diphenylphosphoryl azide, NaHCO3 / dimethylformamide / 15 h / 0 °C
With
2,3,5-trimethyl-pyridine; lithium hydroxide; sodium tetrahydroborate; phosphorus pentachloride; diphenylphosphoranyl azide; tetrabutyl ammonium fluoride; sodium hydride; sodium hydrogencarbonate; triethylamine; sodium iodide;
In
tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; acetonitrile;
DOI:10.1021/jo961114p
![(S)-2-[(2S,6R,7S,9S)-2-(4-Benzyloxy-benzyl)-9-(3-benzyloxycarbonylamino-propyl)-10-oxo-4-oxa-1,8-diaza-bicyclo[5.3.1]undec-6-ylamino]-3-(1H-indol-3-yl)-propionic acid](/Databaselist/images/loading.webp)
