Technology Process of (1R,3S)-8-Acetyl-1-benzyloxycarbonylamino-1-methyl-5-oxo-6-(toluene-3-sulfonylamino)-1,2,3,5-tetrahydro-indolizine-3-carboxylic acid methyl ester
There total 17 articles about (1R,3S)-8-Acetyl-1-benzyloxycarbonylamino-1-methyl-5-oxo-6-(toluene-3-sulfonylamino)-1,2,3,5-tetrahydro-indolizine-3-carboxylic acid methyl 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:
-
Multi-step reaction with 17 steps
1: 90 percent / KHMDS / toluene / -78 °C
2: 92 percent / LHMDS / tetrahydrofuran / -78 °C
3: 90 percent / TFA / CH2Cl2
4: 89 percent / LHMDS / tetrahydrofuran / -78 °C
5: Rh2(OAc)4 / benzene / 90 °C
6: PTSA / CH2Cl2 / 50 °C
7: 55 percent / POCl3 / pyridine
8: TFA / CH2Cl2
9: Et3N / tetrahydrofuran / -5 °C
10: NaN3 / tetrahydrofuran / -5 °C
11: toluene / 90 °C
12: H2 / Pd/C / methanol
13: Et3N / tetrahydrofuran / -5 °C
14: NaN3 / tetrahydrofuran / -5 °C
15: toluene / 90 °C
16: TFA / CH2Cl2
17: 65 percent / Et3N / pyridine
With
sodium azide; hydrogen; potassium hexamethylsilazane; toluene-4-sulfonic acid; triethylamine; trifluoroacetic acid; lithium hexamethyldisilazane; trichlorophosphate;
dirhodium tetraacetate; palladium on activated charcoal;
In
tetrahydrofuran; pyridine; methanol; dichloromethane; toluene; benzene;
11: Curtius rearrangement / 15: Curtius rearrangement;
DOI:10.1016/S0040-4039(02)02447-4
- Guidance literature:
-
Multi-step reaction with 16 steps
1: 92 percent / LHMDS / tetrahydrofuran / -78 °C
2: 90 percent / TFA / CH2Cl2
3: 89 percent / LHMDS / tetrahydrofuran / -78 °C
4: Rh2(OAc)4 / benzene / 90 °C
5: PTSA / CH2Cl2 / 50 °C
6: 55 percent / POCl3 / pyridine
7: TFA / CH2Cl2
8: Et3N / tetrahydrofuran / -5 °C
9: NaN3 / tetrahydrofuran / -5 °C
10: toluene / 90 °C
11: H2 / Pd/C / methanol
12: Et3N / tetrahydrofuran / -5 °C
13: NaN3 / tetrahydrofuran / -5 °C
14: toluene / 90 °C
15: TFA / CH2Cl2
16: 65 percent / Et3N / pyridine
With
sodium azide; hydrogen; toluene-4-sulfonic acid; triethylamine; trifluoroacetic acid; lithium hexamethyldisilazane; trichlorophosphate;
dirhodium tetraacetate; palladium on activated charcoal;
In
tetrahydrofuran; pyridine; methanol; dichloromethane; toluene; benzene;
10: Curtius rearrangement / 14: Curtius rearrangement;
DOI:10.1016/S0040-4039(02)02447-4