Technology Process of (cis,4R,5R,12R,13S)-5-tert-butyldiphenylsilyloxytricosa-12,13-isopropylidenedioxy-8-en-1,4-olide
There total 23 articles about (cis,4R,5R,12R,13S)-5-tert-butyldiphenylsilyloxytricosa-12,13-isopropylidenedioxy-8-en-1,4-olide 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:
-
(4R,5S)-4,5-isopropylidenedioxypentadecan-1-yltriphenylphosphoniumiodide;
With
potassium hexamethylsilazane;
In
tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide;
at -78 ℃;
(4R,5R)-tert-butyldiphenylsilyloxyoctan-1-al-5,8-olide;
In
tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide;
at -78 - 20 ℃;
Further stages.;
DOI:10.1021/jo000500a
- Guidance literature:
-
Multi-step reaction with 7 steps
1.1: AD-mix-β; MeSO2NH2 / 2-methyl-propan-2-ol; H2O / 16 h / 0 °C
2.1: KOH / H2O; methanol / 2 h / 60 °C
3.1: 13.52 g / TsOH / CH2Cl2
4.1: 94 percent / imidazole / dimethylformamide / 16 h / 20 °C
5.1: 98 percent / H2; propionic acid / methanol / 16 h
6.1: PCC; Celite / CH2Cl2 / 2 h / 20 °C
7.1: KHMDS / hexamethylphosphoric acid triamide; tetrahydrofuran / -78 °C
7.2: 71 percent / hexamethylphosphoric acid triamide; tetrahydrofuran / -78 - 20 °C
With
1H-imidazole; potassium hydroxide; methanesulfonamide; AD-mix-β; Celite; hydrogen; potassium hexamethylsilazane; toluene-4-sulfonic acid; propionic acid; pyridinium chlorochromate;
In
tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;
1.1: Sharpless asymmetric hydroxylation / 2.1: Hydrolysis / 3.1: Cyclization / 4.1: Substitution / 5.1: Catalytic hydrogenation / 6.1: Oxidation / 7.1: deprotonation / 7.2: Wittig reaction;
DOI:10.1021/jo000500a
- Guidance literature:
-
Multi-step reaction with 3 steps
1.1: 98 percent / H2; propionic acid / methanol / 16 h
2.1: PCC; Celite / CH2Cl2 / 2 h / 20 °C
3.1: KHMDS / hexamethylphosphoric acid triamide; tetrahydrofuran / -78 °C
3.2: 71 percent / hexamethylphosphoric acid triamide; tetrahydrofuran / -78 - 20 °C
With
Celite; hydrogen; potassium hexamethylsilazane; propionic acid; pyridinium chlorochromate;
In
tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane;
1.1: Catalytic hydrogenation / 2.1: Oxidation / 3.1: deprotonation / 3.2: Wittig reaction;
DOI:10.1021/jo000500a
