Technology Process of (2S,3S,4R,9Z)-2-(t-butoxycarbonyl)amino-1-(t-butyldiphenylsilyloxy)-3-(4-methoxybenzyloxy)-9-docosen-4-ol
There total 12 articles about (2S,3S,4R,9Z)-2-(t-butoxycarbonyl)amino-1-(t-butyldiphenylsilyloxy)-3-(4-methoxybenzyloxy)-9-docosen-4-ol 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:
-
(4Z)-1-bromo-4-heptadecene;
With
magnesium;
In
diethyl ether;
With
1,4-dioxane;
In
diethyl ether;
2-(t-butoxycarbonyl)amino-1-O-(t-butyldiphenylsilyl)-2-deoxy-3-O-(4-methoxybenzyl)-D-4,5-anhydroribitol;
In
diethyl ether;
at 0 - 20 ℃;
for 3h;
DOI:10.1246/bcsj.71.259
- Guidance literature:
-
Multi-step reaction with 10 steps
1.1: acetic acid / H2O / 2 h / 50 °C
2.1: 3.48 g / p-toluenesulfonic acid monohydrate / 5 h / 20 °C
3.1: 100 percent / imidazole / dimethylformamide / 10.2 h / 0 - 20 °C
4.1: 100 percent / triethylamine / CH2Cl2 / 1.17 h / 0 - 20 °C
5.1: 75 percent / acetic acid / H2O / 17 h / 50 °C
6.1: lead(IV) acetate / benzene / 0.5 h / 20 °C
7.1: NaBH4 / methanol / 1 h / 0 - 20 °C
8.1: 768 mg / sodium methoxide / methanol / 4 h / 0 - 20 °C
9.1: 75 percent / H2 / Pd-BaSO4 / ethyl acetate; ethanol / 30 h / 20 °C / 760 Torr
10.1: Mg / diethyl ether
10.2: 1,4-dioxane / diethyl ether
10.3: 57 percent / CuCN / diethyl ether / 3 h / 0 - 20 °C
With
1H-imidazole; lead(IV) acetate; sodium tetrahydroborate; hydrogen; sodium methylate; toluene-4-sulfonic acid; magnesium; acetic acid; triethylamine;
palladium on barium sulfate;
In
methanol; diethyl ether; ethanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; benzene;
1.1: Hydrolysis / 2.1: Cyclization / 3.1: silylation / 4.1: mesylation / 5.1: Hydrolysis / 6.1: Oxidation / 7.1: Reduction / 8.1: Cyclization / 9.1: Hydrogenation / 10.1: Metallation / 10.2: Disproportionation / 10.3: Addition;
DOI:10.1246/bcsj.71.259
- Guidance literature:
-
Multi-step reaction with 4 steps
1.1: butyllithium / tetrahydrofuran; hexane / 3 h / -78 - 0 °C
1.2: 67 percent / HMPA / tetrahydrofuran; hexane / 2.5 h / -40 - 20 °C
2.1: 85 percent / H2 / Lindlar catalyst / ethyl acetate / 72 h / 20 °C / 760 Torr
3.1: 92 percent / triphenylphosphine; N-bromosuccinimide / dimethylformamide / 2 h / 0 °C
4.1: Mg / diethyl ether
4.2: 1,4-dioxane / diethyl ether
4.3: 57 percent / CuCN / diethyl ether / 3 h / 0 - 20 °C
With
N-Bromosuccinimide; n-butyllithium; hydrogen; magnesium; triphenylphosphine;
Lindlar's catalyst;
In
tetrahydrofuran; diethyl ether; hexane; ethyl acetate; N,N-dimethyl-formamide;
1.1: Metallation / 1.2: Alkylation / 2.1: Catalytic hydrogenation / 3.1: Bromination / 4.1: Metallation / 4.2: Disproportionation / 4.3: Addition;
DOI:10.1246/bcsj.71.259
