Technology Process of (1R,2R,3S,6R,7S,8S)-3-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxy-7-methoxy-8-methyl-5,9-dioxa-tricyclo[6.2.1.02,6]undecan-10-one
There total 17 articles about (1R,2R,3S,6R,7S,8S)-3-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxy-7-methoxy-8-methyl-5,9-dioxa-tricyclo[6.2.1.02,6]undecan-10-one 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 15 steps
1: Et3N, DMAP / CH2Cl2 / -10 - 22 °C
2: NaH / tetrahydrofuran / 0 - 22 °C
3: p-TsOH / methanol / 14 h / 22 °C
4: Et3N, DMAP / CH2Cl2 / -78 - -40 °C
5: NaH / dimethylformamide / 0 °C
6: LiOH, H2O / tetrahydrofuran
7: PCC-Al2O3 / -60 °C
8: 83 percent / tetrahydrofuran / -78 °C
9: 79 percent / PCC-Al2O3
10: 70 percent / tetrahydrofuran / -78 °C
11: 1.) O3, pyridine, 2.) Ph3P / 1.) CH2Cl2; 2.) CH2Cl2
12: PCC-Al2O3
13: 81 percent / H2 / Pd-black / ethanol
14: 85 percent / PCC-Al2O3 / CH2Cl2 / 12 h / 40 °C
15: 85 percent / LDA / tetrahydrofuran / -78 °C
With
pyridine; dmap; lithium hydroxide; pyridinium chlorochromate absorbed on neutral alumina; water; hydrogen; sodium hydride; toluene-4-sulfonic acid; ozone; triethylamine; triphenylphosphine; lithium diisopropyl amide;
palladium;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/0040-4039(88)85177-3
- Guidance literature:
-
Multi-step reaction with 14 steps
1: NaH / tetrahydrofuran / 0 - 22 °C
2: p-TsOH / methanol / 14 h / 22 °C
3: Et3N, DMAP / CH2Cl2 / -78 - -40 °C
4: NaH / dimethylformamide / 0 °C
5: LiOH, H2O / tetrahydrofuran
6: PCC-Al2O3 / -60 °C
7: 83 percent / tetrahydrofuran / -78 °C
8: 79 percent / PCC-Al2O3
9: 70 percent / tetrahydrofuran / -78 °C
10: 1.) O3, pyridine, 2.) Ph3P / 1.) CH2Cl2; 2.) CH2Cl2
11: PCC-Al2O3
12: 81 percent / H2 / Pd-black / ethanol
13: 85 percent / PCC-Al2O3 / CH2Cl2 / 12 h / 40 °C
14: 85 percent / LDA / tetrahydrofuran / -78 °C
With
pyridine; dmap; lithium hydroxide; pyridinium chlorochromate absorbed on neutral alumina; water; hydrogen; sodium hydride; toluene-4-sulfonic acid; ozone; triethylamine; triphenylphosphine; lithium diisopropyl amide;
palladium;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/0040-4039(88)85177-3
