Technology Process of (2S,5'S)-5'-(Benzyloxycarbamoyl-methyl)-4-((R)-1-ethoxycarbonyl-ethyl)-2,5'-diisobutyl-3,4'-dioxo-2,3,4',5'-tetrahydro-[2,3']bipyrrolyl-1,1'-dicarboxylic acid dibenzyl ester
There total 13 articles about (2S,5'S)-5'-(Benzyloxycarbamoyl-methyl)-4-((R)-1-ethoxycarbonyl-ethyl)-2,5'-diisobutyl-3,4'-dioxo-2,3,4',5'-tetrahydro-[2,3']bipyrrolyl-1,1'-dicarboxylic acid dibenzyl ester which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
(2S,5'S)-5'-Carboxymethyl-4-((R)-1-ethoxycarbonyl-ethyl)-2,5'-diisobutyl-3,4'-dioxo-2,3,4',5'-tetrahydro-[2,3']bipyrrolyl-1,1'-dicarboxylic acid dibenzyl ester;
With
benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride;
In
dichloromethane;
at 0 ℃;
for 0.5h;
O-benzylhydoxylamine hydrochloride;
With
N-ethyl-N,N-diisopropylamine;
In
dichloromethane;
for 4h;
Further stages.;
DOI:10.1021/ol000254p
- Guidance literature:
-
Multi-step reaction with 12 steps
1.1: 99 percent / iPr2NEt / CH2Cl2 / 2 h / 0 °C
2.1: 71 percent / Ph3P / CH2Cl2 / -78 - 20 °C
3.1: toluene / 0.25 h
3.2: 93 percent / KHMDS / tetrahydrofuran; toluene / 0.33 h
4.1: 99 percent / p-TsOH / tetrahydrofuran; H2O / 4 h / 50 °C
5.1: toluene / 0.25 h
5.2: 84 percent / KHMDS / tetrahydrofuran; toluene / 0.75 h
6.1: 80 percent / NaHMDS / tetrahydrofuran / 0.25 h / -78 °C
7.1: 93 percent / p-TsOH / methanol; tetrahydrofuran / 2.5 h / 40 °C
8.1: Dess-Martin periodinane / CH2Cl2 / 1.5 h
8.2: 81 percent / NaClO2; Na2H2PO4 / various solvent(s); 2-methyl-propan-2-ol; H2O / 2 h
9.1: 58 percent / diisopropylcarbodiimide; DMAP; 1-hydroxybenzotriazol / dimethylformamide / 7 h
10.1: p-TsOH / tetrahydrofuran; H2O / 3 h / 40 °C
11.1: 40 mg / NaClO2; Na2H2PO4 / 2-methyl-propan-2-ol; H2O; various solvent(s) / 1.5 h / 0 °C
12.1: EDCI*HCl; 1-hydroxybenzotriazole / CH2Cl2 / 0.5 h / 0 °C
12.2: 90 percent / diisopropylethylamine / CH2Cl2 / 4 h
With
dmap; sodium chlorite; Na2H2PO4; sodium hexamethyldisilazane; benzotriazol-1-ol; Dess-Martin periodane; toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; diisopropyl-carbodiimide;
In
tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;
1.1: Silylation / 2.1: Ozonolysis / 3.1: Condensation / 3.2: Dehydration / 4.1: Hydrolysis / 5.1: Condensation / 5.2: Dehydration / 6.1: Acetylation / 7.1: Hydrolysis / 8.1: Oxidation / 8.2: Oxidation / 9.1: Esterification / 10.1: Hydrolysis / 11.1: Oxidation / 12.1: Condensation / 12.2: Condensation;
DOI:10.1021/ol000254p
- Guidance literature:
-
Multi-step reaction with 10 steps
1.1: toluene / 0.25 h
1.2: 93 percent / KHMDS / tetrahydrofuran; toluene / 0.33 h
2.1: 99 percent / p-TsOH / tetrahydrofuran; H2O / 4 h / 50 °C
3.1: toluene / 0.25 h
3.2: 84 percent / KHMDS / tetrahydrofuran; toluene / 0.75 h
4.1: 80 percent / NaHMDS / tetrahydrofuran / 0.25 h / -78 °C
5.1: 93 percent / p-TsOH / methanol; tetrahydrofuran / 2.5 h / 40 °C
6.1: Dess-Martin periodinane / CH2Cl2 / 1.5 h
6.2: 81 percent / NaClO2; Na2H2PO4 / various solvent(s); 2-methyl-propan-2-ol; H2O / 2 h
7.1: 58 percent / diisopropylcarbodiimide; DMAP; 1-hydroxybenzotriazol / dimethylformamide / 7 h
8.1: p-TsOH / tetrahydrofuran; H2O / 3 h / 40 °C
9.1: 40 mg / NaClO2; Na2H2PO4 / 2-methyl-propan-2-ol; H2O; various solvent(s) / 1.5 h / 0 °C
10.1: EDCI*HCl; 1-hydroxybenzotriazole / CH2Cl2 / 0.5 h / 0 °C
10.2: 90 percent / diisopropylethylamine / CH2Cl2 / 4 h
With
dmap; sodium chlorite; Na2H2PO4; sodium hexamethyldisilazane; benzotriazol-1-ol; Dess-Martin periodane; toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; diisopropyl-carbodiimide;
In
tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;
1.1: Condensation / 1.2: Dehydration / 2.1: Hydrolysis / 3.1: Condensation / 3.2: Dehydration / 4.1: Acetylation / 5.1: Hydrolysis / 6.1: Oxidation / 6.2: Oxidation / 7.1: Esterification / 8.1: Hydrolysis / 9.1: Oxidation / 10.1: Condensation / 10.2: Condensation;
DOI:10.1021/ol000254p
