Technology Process of (2E,16E,18Z)-(1S,10S,11S,21S,22S,25S,26R)-9-(2,4-Dimethoxy-benzyl)-11-hydroxy-25-methyl-6,8,15-trioxo-9,14-diaza-tricyclo[19.6.0.022,26]heptacosa-2,16,18,23-tetraene-10-carboxylic acid ethyl ester
There total 26 articles about (2E,16E,18Z)-(1S,10S,11S,21S,22S,25S,26R)-9-(2,4-Dimethoxy-benzyl)-11-hydroxy-25-methyl-6,8,15-trioxo-9,14-diaza-tricyclo[19.6.0.022,26]heptacosa-2,16,18,23-tetraene-10-carboxylic acid ethyl 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:
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![(2E,16E,18Z)-(1S,10S,11S,21S,22S,25S,26R)-11-(tert-Butyl-dimethyl-silanyloxy)-9-(2,4-dimethoxy-benzyl)-25-methyl-6,8,15-trioxo-9,14-diaza-tricyclo[19.6.0.0<sup>22,26</sup>]heptacosa-2,16,18,23-tetraene-10-carboxylic acid ethyl ester](/Databaselist/images/loading.webp)
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878003-28-2
(2E,16E,18Z)-(1S,10S,11S,21S,22S,25S,26R)-11-(tert-Butyl-dimethyl-silanyloxy)-9-(2,4-dimethoxy-benzyl)-25-methyl-6,8,15-trioxo-9,14-diaza-tricyclo[19.6.0.022,26]heptacosa-2,16,18,23-tetraene-10-carboxylic acid ethyl ester
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878003-23-7
(2E,16E,18Z)-(1S,10S,11S,21S,22S,25S,26R)-9-(2,4-Dimethoxy-benzyl)-11-hydroxy-25-methyl-6,8,15-trioxo-9,14-diaza-tricyclo[19.6.0.022,26]heptacosa-2,16,18,23-tetraene-10-carboxylic acid ethyl ester
- Guidance literature:
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With
hydrogen fluoride;
In
acetonitrile;
at 0 ℃;
for 7h;
DOI:10.1021/ja057899a
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878003-23-7
(2E,16E,18Z)-(1S,10S,11S,21S,22S,25S,26R)-9-(2,4-Dimethoxy-benzyl)-11-hydroxy-25-methyl-6,8,15-trioxo-9,14-diaza-tricyclo[19.6.0.022,26]heptacosa-2,16,18,23-tetraene-10-carboxylic acid ethyl ester
- Guidance literature:
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Multi-step reaction with 10 steps
1.1: SOCl2; Et3N / CH2Cl2
1.2: NaN3 / dimethylformamide / 55 °C
2.1: CH2Cl2
3.1: H2 / Pd/C / ethyl acetate
4.1: 4 Angstroem molecular sieves / methanol
5.1: NaBH3CN / methanol
6.1: TFA / CH2Cl2
7.1: thiazolidine-2-thione; EDCI; DMAP / Et3N
8.1: NaHMDS / tetrahydrofuran / 0.25 h / -78 °C
8.2: 90 percent / tetrahydrofuran / 0.5 h / -78 - 20 °C
9.1: 65 percent / toluene / 2 h / Heating
10.1: 90 percent / aq. HF / acetonitrile / 7 h / 0 °C
With
thiazolidine-2-thione; dmap; thionyl chloride; 4 A molecular sieve; hydrogen fluoride; hydrogen; sodium hexamethyldisilazane; sodium cyanoborohydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid;
palladium on activated charcoal; triethylamine;
In
tetrahydrofuran; methanol; dichloromethane; ethyl acetate; toluene; acetonitrile;
8.2: Horner-Wadsworth-Emmons reaction;
DOI:10.1021/ja057899a
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878003-23-7
(2E,16E,18Z)-(1S,10S,11S,21S,22S,25S,26R)-9-(2,4-Dimethoxy-benzyl)-11-hydroxy-25-methyl-6,8,15-trioxo-9,14-diaza-tricyclo[19.6.0.022,26]heptacosa-2,16,18,23-tetraene-10-carboxylic acid ethyl ester
- Guidance literature:
-
Multi-step reaction with 9 steps
1.1: CH2Cl2
2.1: H2 / Pd/C / ethyl acetate
3.1: 4 Angstroem molecular sieves / methanol
4.1: NaBH3CN / methanol
5.1: TFA / CH2Cl2
6.1: thiazolidine-2-thione; EDCI; DMAP / Et3N
7.1: NaHMDS / tetrahydrofuran / 0.25 h / -78 °C
7.2: 90 percent / tetrahydrofuran / 0.5 h / -78 - 20 °C
8.1: 65 percent / toluene / 2 h / Heating
9.1: 90 percent / aq. HF / acetonitrile / 7 h / 0 °C
With
thiazolidine-2-thione; dmap; 4 A molecular sieve; hydrogen fluoride; hydrogen; sodium hexamethyldisilazane; sodium cyanoborohydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid;
palladium on activated charcoal; triethylamine;
In
tetrahydrofuran; methanol; dichloromethane; ethyl acetate; toluene; acetonitrile;
7.2: Horner-Wadsworth-Emmons reaction;
DOI:10.1021/ja057899a
