Technology Process of Cryptophycin 53
There total 40 articles about Cryptophycin 53 which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
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Multi-step reaction with 3 steps
1.1: Oxone(R); 1,2:4,5-di-O-(Me2C)-β-D-erythro-hexo-2,3-diulo-2,6-pyranose; potassium carbonate / tetra-n-butylammonium hydrogen sulfate; ethylenediaminetetraacetic acid disodium salt / acetonitrile; H2O / 2 h / 0 °C / pH 10.3 - 10.7
2.1: 4-(dimethylamino)pyridine / CH2Cl2
2.2: 1,3-dicyclohexylcarbodiimide / CH2Cl2
3.1: piperidine / dimethylformamide / 16 h
With
piperidine; dmap; oxone; Shi's ketone; potassium carbonate;
tetra(n-butyl)ammonium hydrogensulfate; disodium ethylenediaminetetraacetic acid;
In
dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;
1.1: Shi epoxidation;
DOI:10.1021/ol025933+
- Guidance literature:
-
Multi-step reaction with 7 steps
1: 78 percent / EDCI; DMAP / CH2Cl2 / 17 h / 23 °C
2: 100 percent / H2 / Pd/C / ethyl acetate / 1.5 h / 23 °C
3: Et3N / tetrahydrofuran / 3.5 h / 23 °C
4: 229 mg / Et3N; DMAP / toluene / 0.5 h / 23 °C
5: CF3COOH / CH2Cl2 / 0 - 20 °C
6: 57 mg / pentafluorophenyl diphenylphosphinate; i-Pr2NEt / dimethylformamide / 12 h / 23 °C
7: m-CPBA / CH2Cl2 / 12 h / 0 - 23 °C
With
dmap; pentafluorophenyl diphenyl-phosphinate; hydrogen; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid;
palladium on activated charcoal;
In
tetrahydrofuran; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo035077v
