Technology Process of (1E,6E,8Z,10Z,14E)-(3S,4R,12S,13S)-13-(tert-butyl-dimethyl-silanyloxy)-1-iodo-3-methoxy-17-(4-methoxy-benzyloxy)-2,4,8,10,12,15-hexamethyl-heptadeca-1,6,8,10,14-pentaen-5-one
There total 21 articles about (1E,6E,8Z,10Z,14E)-(3S,4R,12S,13S)-13-(tert-butyl-dimethyl-silanyloxy)-1-iodo-3-methoxy-17-(4-methoxy-benzyloxy)-2,4,8,10,12,15-hexamethyl-heptadeca-1,6,8,10,14-pentaen-5-one 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:
-
-
942133-19-9
(1E,6E,8Z,10Z,14E)-(3S,4R,12S,13S)-13-(tert-butyl-dimethyl-silanyloxy)-1-iodo-3-methoxy-17-(4-methoxy-benzyloxy)-2,4,8,10,12,15-hexamethyl-heptadeca-1,6,8,10,14-pentaen-5-one
- Guidance literature:
-
C38H61IO6Si;
With
dmap; acetic anhydride;
In
tetrahydrofuran;
at 20 ℃;
for 0.666667h;
With
1,8-diazabicyclo[5.4.0]undec-7-ene;
In
tetrahydrofuran;
for 1h;
Further stages.;
DOI:10.1021/ja071461o
-
-
942133-19-9
(1E,6E,8Z,10Z,14E)-(3S,4R,12S,13S)-13-(tert-butyl-dimethyl-silanyloxy)-1-iodo-3-methoxy-17-(4-methoxy-benzyloxy)-2,4,8,10,12,15-hexamethyl-heptadeca-1,6,8,10,14-pentaen-5-one
- Guidance literature:
-
Multi-step reaction with 9 steps
1.1: sodium meta-periodate / methanol; H2O / 0.67 h / 0 °C
2.1: 18-crown-6; KHMDS / tetrahydrofuran; toluene / 0.25 h / -40 °C
2.2: tetrahydrofuran; toluene / 3 h / -78 °C
3.1: DIBAl-H / CH2Cl2; hexane / 1 h / -78 °C
4.1: MnO2 / CH2Cl2 / 20 h / 20 °C
5.1: 18-crown-6; KHMDS / tetrahydrofuran / 0.25 h / -40 °C
5.2: 87 percent / tetrahydrofuran / 6 h / -78 °C
6.1: DIBAl-H / CH2Cl2; hexane / 1 h / -78 °C
7.1: Dess-Martin periodinane / CH2Cl2 / 1 h / 0 °C
8.1: (c-Hex)2BCl; NEt3 / diethyl ether / 1 h / 0 °C
8.2: diethyl ether / -78 - -30 °C
8.3: aq. H2O2 / diethyl ether; methanol / 1 h / 0 °C / pH 7
9.1: Ac2O; DMAP / tetrahydrofuran / 0.67 h / 20 °C
9.2: DBU / tetrahydrofuran / 1 h
With
dmap; manganese(IV) oxide; sodium periodate; 18-crown-6 ether; dicyclohexylboron chloride; acetic anhydride; potassium hexamethylsilazane; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine;
In
tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; toluene;
2.2: Horner-Wadsworth-Emmons olefination / 5.2: Horner-Wadsworth-Emmons olefination / 8.2: Peterson aldol reaction;
DOI:10.1021/ja071461o
-
-
942133-19-9
(1E,6E,8Z,10Z,14E)-(3S,4R,12S,13S)-13-(tert-butyl-dimethyl-silanyloxy)-1-iodo-3-methoxy-17-(4-methoxy-benzyloxy)-2,4,8,10,12,15-hexamethyl-heptadeca-1,6,8,10,14-pentaen-5-one
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: 18-crown-6; KHMDS / tetrahydrofuran; toluene / 0.25 h / -40 °C
1.2: tetrahydrofuran; toluene / 3 h / -78 °C
2.1: DIBAl-H / CH2Cl2; hexane / 1 h / -78 °C
3.1: MnO2 / CH2Cl2 / 20 h / 20 °C
4.1: 18-crown-6; KHMDS / tetrahydrofuran / 0.25 h / -40 °C
4.2: 87 percent / tetrahydrofuran / 6 h / -78 °C
5.1: DIBAl-H / CH2Cl2; hexane / 1 h / -78 °C
6.1: Dess-Martin periodinane / CH2Cl2 / 1 h / 0 °C
7.1: (c-Hex)2BCl; NEt3 / diethyl ether / 1 h / 0 °C
7.2: diethyl ether / -78 - -30 °C
7.3: aq. H2O2 / diethyl ether; methanol / 1 h / 0 °C / pH 7
8.1: Ac2O; DMAP / tetrahydrofuran / 0.67 h / 20 °C
8.2: DBU / tetrahydrofuran / 1 h
With
dmap; manganese(IV) oxide; 18-crown-6 ether; dicyclohexylboron chloride; acetic anhydride; potassium hexamethylsilazane; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine;
In
tetrahydrofuran; diethyl ether; hexane; dichloromethane; toluene;
1.2: Horner-Wadsworth-Emmons olefination / 4.2: Horner-Wadsworth-Emmons olefination / 7.2: Peterson aldol reaction;
DOI:10.1021/ja071461o
