Technology Process of (2E,4S,5R,6S,8R)-5-(tert-butyl-dimethyl-silanyloxy)-6-methoxy-9-(3-nitro-2,5,6-trimethoxy-phenyl)-2,4,8-trimethyl-non-2-enal
There total 14 articles about (2E,4S,5R,6S,8R)-5-(tert-butyl-dimethyl-silanyloxy)-6-methoxy-9-(3-nitro-2,5,6-trimethoxy-phenyl)-2,4,8-trimethyl-non-2-enal 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
oxalyl dichloride; dimethyl sulfoxide; triethylamine;
In
dichloromethane;
at -78 - -50 ℃;
DOI:10.1021/jo034870l
- Guidance literature:
-
Multi-step reaction with 9 steps
1.1: NaHMDS / diethyl ether / 1 h / 0 - 20 °C
1.2: 98 percent / diethyl ether / 2 h / 20 °C
2.1: 99 percent / aq. HF / acetonitrile / 3 h / 20 °C
3.1: BH3*THF / tetrahydrofuran / 2.25 h / -5 °C
3.2: 78 percent / aq. NaOH; aq. H2O2 / tetrahydrofuran; methanol / 2 h / 0 - 20 °C
4.1: 90 percent / 2,6-lutidine / CH2Cl2 / 2 h / 0 - 20 °C
5.1: 80 percent / CSA / methanol; CH2Cl2 / 2.5 h / 0 °C
6.1: 85 percent / Dess-Martin periodinane / CH2Cl2 / 3 h / 0 °C
7.1: 93 percent / toluene / 7 h / 90 °C
8.1: 86 percent / DIBAL-H / tetrahydrofuran; toluene / 4 h / -78 °C
9.1: 89 percent / oxalyl chloride; DMSO; Et3N / CH2Cl2 / -78 - -50 °C
With
2,6-dimethylpyridine; borane-THF; oxalyl dichloride; camphor-10-sulfonic acid; hydrogen fluoride; sodium hexamethyldisilazane; diisobutylaluminium hydride; Dess-Martin periodane; dimethyl sulfoxide; triethylamine;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene; acetonitrile;
1.2: Wittig reaction;
DOI:10.1021/jo034870l
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: 99 percent / aq. HF / acetonitrile / 3 h / 20 °C
2.1: BH3*THF / tetrahydrofuran / 2.25 h / -5 °C
2.2: 78 percent / aq. NaOH; aq. H2O2 / tetrahydrofuran; methanol / 2 h / 0 - 20 °C
3.1: 90 percent / 2,6-lutidine / CH2Cl2 / 2 h / 0 - 20 °C
4.1: 80 percent / CSA / methanol; CH2Cl2 / 2.5 h / 0 °C
5.1: 85 percent / Dess-Martin periodinane / CH2Cl2 / 3 h / 0 °C
6.1: 93 percent / toluene / 7 h / 90 °C
7.1: 86 percent / DIBAL-H / tetrahydrofuran; toluene / 4 h / -78 °C
8.1: 89 percent / oxalyl chloride; DMSO; Et3N / CH2Cl2 / -78 - -50 °C
With
2,6-dimethylpyridine; borane-THF; oxalyl dichloride; camphor-10-sulfonic acid; hydrogen fluoride; diisobutylaluminium hydride; Dess-Martin periodane; dimethyl sulfoxide; triethylamine;
In
tetrahydrofuran; methanol; dichloromethane; toluene; acetonitrile;
DOI:10.1021/jo034870l
