Technology Process of (5Z,7E)-(1R,3S)-1,3-bis[(tert-butyldimethylsilyl)oxy]-25-[(trimethylsilyl)oxy]-9,10-secocholesta-5,7,10(19)-trien-16α-yl hydrogen glutarate
There total 12 articles about (5Z,7E)-(1R,3S)-1,3-bis[(tert-butyldimethylsilyl)oxy]-25-[(trimethylsilyl)oxy]-9,10-secocholesta-5,7,10(19)-trien-16α-yl hydrogen glutarate 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
dmap;
In
dichloromethane;
at 4 ℃;
for 72h;
DOI:10.1021/jo026061s
- Guidance literature:
-
Multi-step reaction with 12 steps
1.1: 68 percent / POCl3 / pyridine / 0 - 5 °C
2.1: 59 percent / BF3*OEt2 / CH2Cl2 / 0.13 h / 20 °C
3.1: 95 percent / pyridine / CH2Cl2 / 0 - 20 °C
4.1: 66 percent / Mg; Li2CuCl4 / tetrahydrofuran / 1 h / 0 °C
5.1: BH3*THF / tetrahydrofuran; hexane / 0 °C
5.2: 68 percent / 30percent H2O2; aq. NaOH / tetrahydrofuran / 2 h / 0 °C
6.1: 74 percent / pyridine / 3 h / 20 °C
7.1: 64 percent / 40percent aq. HF / acetonitrile / 8 h / 20 °C
8.1: 83 percent / PDC / CH2Cl2 / 6 h / 20 °C
9.1: 90 percent / DMAP; Et3N / CH2Cl2 / 0 - 20 °C
10.1: n-BuLi / tetrahydrofuran / 0.42 h / -78 °C
10.2: 89 percent / tetrahydrofuran / -78 - 20 °C
11.1: 55 percent / KOH / methanol / 6 h / 40 °C
12.1: 39 percent / DMAP / CH2Cl2 / 72 h / 4 °C
With
pyridine; dmap; potassium hydroxide; dipyridinium dichromate; n-butyllithium; borane-THF; dilithium tetrachlorocuprate; boron trifluoride diethyl etherate; magnesium; triethylamine; trichlorophosphate;
In
tetrahydrofuran; pyridine; methanol; hexane; dichloromethane; acetonitrile;
DOI:10.1021/jo026061s
- Guidance literature:
-
Multi-step reaction with 11 steps
1.1: 59 percent / BF3*OEt2 / CH2Cl2 / 0.13 h / 20 °C
2.1: 95 percent / pyridine / CH2Cl2 / 0 - 20 °C
3.1: 66 percent / Mg; Li2CuCl4 / tetrahydrofuran / 1 h / 0 °C
4.1: BH3*THF / tetrahydrofuran; hexane / 0 °C
4.2: 68 percent / 30percent H2O2; aq. NaOH / tetrahydrofuran / 2 h / 0 °C
5.1: 74 percent / pyridine / 3 h / 20 °C
6.1: 64 percent / 40percent aq. HF / acetonitrile / 8 h / 20 °C
7.1: 83 percent / PDC / CH2Cl2 / 6 h / 20 °C
8.1: 90 percent / DMAP; Et3N / CH2Cl2 / 0 - 20 °C
9.1: n-BuLi / tetrahydrofuran / 0.42 h / -78 °C
9.2: 89 percent / tetrahydrofuran / -78 - 20 °C
10.1: 55 percent / KOH / methanol / 6 h / 40 °C
11.1: 39 percent / DMAP / CH2Cl2 / 72 h / 4 °C
With
pyridine; dmap; potassium hydroxide; dipyridinium dichromate; n-butyllithium; borane-THF; dilithium tetrachlorocuprate; boron trifluoride diethyl etherate; magnesium; triethylamine;
In
tetrahydrofuran; pyridine; methanol; hexane; dichloromethane; acetonitrile;
DOI:10.1021/jo026061s
