Technology Process of (E)-(2S,3S,4S,5R,6S)-10-Benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-2-(4-methoxy-benzyloxymethyl)-4,6,8-trimethyl-dec-8-ene-3,5-diol
There total 19 articles about (E)-(2S,3S,4S,5R,6S)-10-Benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-2-(4-methoxy-benzyloxymethyl)-4,6,8-trimethyl-dec-8-ene-3,5-diol 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:
-
(E)-(2S,4S,5R,6S)-10-Benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-2-(4-methoxy-benzyloxymethyl)-4,6,8-trimethyl-dec-8-en-3-one;
With
diethyl methoxy borane;
In
tetrahydrofuran; methanol;
at 20 ℃;
for 0.25h;
With
sodium tetrahydroborate;
In
tetrahydrofuran; methanol;
at -78 ℃;
for 48h;
DOI:10.1021/ol049219z
- Guidance literature:
-
Multi-step reaction with 5 steps
1.1: 68 percent / PdCl2[P(o-Tol)3]2 / tetrahydrofuran / 96 h / 20 °C
2.1: 96 percent / DIBAL / CH2Cl2; hexane / -78 - 45 °C
3.1: 100 percent / Dess-Martin periodinane / CH2Cl2 / 0.33 h / 20 °C
4.1: Sn(OTf)2; Et3N / CH2Cl2 / 3 h / -78 °C
4.2: 77 percent / CH2Cl2 / 6 h / -78 °C
5.1: diethylmethoxyborane / tetrahydrofuran; methanol / 0.25 h / 20 °C
5.2: 73 percent / NaBH4 / tetrahydrofuran; methanol / 48 h / -78 °C
With
tin(II) trifluoromethanesulfonate; diethyl methoxy borane; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine;
dichlorobis(tri-O-tolylphosphine)palladium;
In
tetrahydrofuran; methanol; hexane; dichloromethane;
4.2: Paterson's stereoselective aldol reaction;
DOI:10.1021/ol049219z
- Guidance literature:
-
Multi-step reaction with 2 steps
1: 80 percent / Sn(OTf)2; triethylamine
2: Et2BOMe; NaBH4
With
sodium tetrahydroborate; tin(II) trifluoromethanesulfonate; diethyl methoxy borane; triethylamine;
DOI:10.1016/j.tetlet.2005.07.029
