Technology Process of [(6Z,8E)-(3S,11S,15R,17S)-3-(tert-butyldimethylsilanyloxymethyl)-9,11,17-trimethyl-5,13-dioxo-4,12-dioxa-20-thia-21-azabicyclo[16.2.1]heneicosa-1(21),6,8,18-tetraen-15-yl]carbamic acid 2,2,2-trichloro-1,1-dimethyl ester
There total 1 articles about [(6Z,8E)-(3S,11S,15R,17S)-3-(tert-butyldimethylsilanyloxymethyl)-9,11,17-trimethyl-5,13-dioxo-4,12-dioxa-20-thia-21-azabicyclo[16.2.1]heneicosa-1(21),6,8,18-tetraen-15-yl]carbamic acid 2,2,2-trichloro-1,1-dimethyl ester 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:
-
-
693790-26-0
[(6Z,8E)-(3S,11S,15R,17S)-3-(tert-butyldimethylsilanyloxymethyl)-9,11,17-trimethyl-5,13-dioxo-4,12-dioxa-20-thia-21-azabicyclo[16.2.1]heneicosa-1(21),6,8,18-tetraen-15-yl]carbamic acid 2,2,2-trichloro-1,1-dimethyl ester
- Guidance literature:
-
(Z)-3-tributylstannylpropenoic acid;
With
2,4,6-trichlorobenzoyl chloride; triethylamine;
In
tetrahydrofuran;
at 20 ℃;
for 1h;
(3R,5S)-5-{2-[(S)-3-(tert-butyldimethylsilanyloxy)-2-hydroxypropyl]thiazol-4-yl}-3-(2,2,2-trichloro-1,1-dimethylethoxycarbonylamino)hexanoic acid (E)-(S)-4-iodo-1,3-dimethylbut-3-enyl ester;
With
dmap;
In
toluene;
at -30 ℃;
for 4h;
With
triphenyl-arsane;
bis(dibenzylideneacetone)-palladium(0);
In
N,N-dimethyl-formamide;
at 60 ℃;
for 1h;
DOI:10.1139/v03-199
-
-
693790-26-0
[(6Z,8E)-(3S,11S,15R,17S)-3-(tert-butyldimethylsilanyloxymethyl)-9,11,17-trimethyl-5,13-dioxo-4,12-dioxa-20-thia-21-azabicyclo[16.2.1]heneicosa-1(21),6,8,18-tetraen-15-yl]carbamic acid 2,2,2-trichloro-1,1-dimethyl ester
- Guidance literature:
-
Multi-step reaction with 6 steps
1: 78 percent / TBAF / tetrahydrofuran / 20 h / 20 °C
2: 70 percent / Dess-Martin periodinane / CH2Cl2 / 3.5 h / 0 - 20 °C
3: 73 percent / benzene / 3 h / Heating
4: 68 percent / CrCl2 / tetrahydrofuran / 1.5 h / 20 °C
5: 73 percent / aq. NH4OAc / Cd/Pd / tetrahydrofuran / 3 h / 20 °C
With
chromium dichloride; ammonium acetate; tetrabutyl ammonium fluoride; Dess-Martin periodane;
Cd/Pd;
In
tetrahydrofuran; dichloromethane; benzene;
DOI:10.1139/v03-199