Technology Process of (5S,8S,8aR)-8-Benzyloxy-3-oxo-hexahydro-oxazolo[3,4-a]pyridine-5-carbaldehyde
There total 10 articles about (5S,8S,8aR)-8-Benzyloxy-3-oxo-hexahydro-oxazolo[3,4-a]pyridine-5-carbaldehyde 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 9 steps
1: 81 percent / (COCl)2, DMSO, Et3N / CH2Cl2 / -78 °C
2: 88 percent / CH2Cl2
3: 94 percent / DIBALH / tetrahydrofuran
4: 80 percent / Ti(i-PrO)4, L-DIPT, t-BuOOH / CH2Cl2 / -23 °C
5: 2.) K2CO3, (C8H17)3NMeCl / 1.) THF, room temperature, 2.) MeCN
6: 72 percent / PdCl2(CH2CN)2 / tetrahydrofuran / Ambient temperature
7: 95 percent / aq. K2CO3 / methanol / Ambient temperature
8: 97 percent / NaH, Bu4NI / tetrahydrofuran
9: 1.) O3, 2.) Me2S / 1.) CH2Cl2
With
titanium(IV) isopropylate; tert.-butylhydroperoxide; oxalyl dichloride; dimethylsulfide; L-(+)-diisopropyl tartrate; (C8H17)3NMeCl; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; potassium carbonate; ozone; dimethyl sulfoxide; triethylamine;
dichloro bis(acetonitrile) palladium(II);
In
tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/jo961951r
- Guidance literature:
-
Multi-step reaction with 10 steps
1: 84 percent / H2 / Lindlar catalyst / ethyl acetate
2: 81 percent / (COCl)2, DMSO, Et3N / CH2Cl2 / -78 °C
3: 88 percent / CH2Cl2
4: 94 percent / DIBALH / tetrahydrofuran
5: 80 percent / Ti(i-PrO)4, L-DIPT, t-BuOOH / CH2Cl2 / -23 °C
6: 2.) K2CO3, (C8H17)3NMeCl / 1.) THF, room temperature, 2.) MeCN
7: 72 percent / PdCl2(CH2CN)2 / tetrahydrofuran / Ambient temperature
8: 95 percent / aq. K2CO3 / methanol / Ambient temperature
9: 97 percent / NaH, Bu4NI / tetrahydrofuran
10: 1.) O3, 2.) Me2S / 1.) CH2Cl2
With
titanium(IV) isopropylate; tert.-butylhydroperoxide; oxalyl dichloride; dimethylsulfide; L-(+)-diisopropyl tartrate; (C8H17)3NMeCl; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; potassium carbonate; ozone; dimethyl sulfoxide; triethylamine;
dichloro bis(acetonitrile) palladium(II); Lindlar's catalyst;
In
tetrahydrofuran; methanol; dichloromethane; ethyl acetate;
DOI:10.1021/jo961951r
- Guidance literature:
-
Multi-step reaction with 7 steps
1: 94 percent / DIBALH / tetrahydrofuran
2: 80 percent / Ti(i-PrO)4, L-DIPT, t-BuOOH / CH2Cl2 / -23 °C
3: 2.) K2CO3, (C8H17)3NMeCl / 1.) THF, room temperature, 2.) MeCN
4: 72 percent / PdCl2(CH2CN)2 / tetrahydrofuran / Ambient temperature
5: 95 percent / aq. K2CO3 / methanol / Ambient temperature
6: 97 percent / NaH, Bu4NI / tetrahydrofuran
7: 1.) O3, 2.) Me2S / 1.) CH2Cl2
With
titanium(IV) isopropylate; tert.-butylhydroperoxide; dimethylsulfide; L-(+)-diisopropyl tartrate; (C8H17)3NMeCl; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; potassium carbonate; ozone;
dichloro bis(acetonitrile) palladium(II);
In
tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/jo961951r
