Technology Process of (2S,4R)-13-Hydroxy-3,6,15-trioxatetracyclo[14.2.2.110,14.02,4]henicosa-10,12,14(21),16,18(1),19-hexaene-7-one
There total 15 articles about (2S,4R)-13-Hydroxy-3,6,15-trioxatetracyclo[14.2.2.110,14.02,4]henicosa-10,12,14(21),16,18(1),19-hexaene-7-one which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
hydrogen;
palladium on activated charcoal;
In
ethyl acetate;
for 3h;
Ambient temperature;
DOI:10.1016/0040-4039(95)01987-S
- Guidance literature:
-
Multi-step reaction with 10 steps
1: 93 percent / benzene / Ambient temperature
2: 97 percent / H2 / 5 percent Pd/C / benzene / 5 h / Ambient temperature
3: 78 percent / CuBr*Me2S, K2CO3, pyridine / 6 h / 140 °C
4: 87 percent / K3Fe(CN)6, K2CO3, K2OsO2(OH)4, (DHQD)2PHAL / 2-methyl-propan-2-ol; H2O / 12 h / 0 °C
5: 97 percent / imidazole / dimethylformamide / 3 h / Ambient temperature
6: 1.) LiOH, 2.) DIBAL / 1.) THF/MeOH, 0 deg C -> RT, 2 h, 2.) CH2Cl2, -78 deg C, 10 min
7: 81 percent / DEAD, Ph3P / toluene / 6 h / 45 °C
8: 94 percent / TBAF / tetrahydrofuran / 3 h / Ambient temperature
9: 87 percent / DEAD, Ph3P / dimethylformamide / 0.67 h / 145 °C
10: 95 percent / H2 / 10 percent Pd/C / ethyl acetate / 3 h / Ambient temperature
With
pyridine; 1H-imidazole; lithium hydroxide; potassium dioxotetrahydroxoosmate(VI); copper(I) bromide dimethylsulfide complex; tetrabutyl ammonium fluoride; hydrogen; diisobutylaluminium hydride; potassium carbonate; 1,4-bis(9-O-dihydroquinidine)phthalazine; triphenylphosphine; potassium hexacyanoferrate(III); diethylazodicarboxylate;
palladium on activated charcoal;
In
tetrahydrofuran; water; ethyl acetate; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; benzene;
DOI:10.1016/0040-4039(95)01987-S
- Guidance literature:
-
Multi-step reaction with 10 steps
1: 97 percent / DIBAL / CH2Cl2 / 0.33 h / -78 °C
2: 87 percent / pyridine / dimethylformamide / 6 h / 0 deg C -> RT
3: 78 percent / CuBr*Me2S, K2CO3, pyridine / 6 h / 140 °C
4: 87 percent / K3Fe(CN)6, K2CO3, K2OsO2(OH)4, (DHQD)2PHAL / 2-methyl-propan-2-ol; H2O / 12 h / 0 °C
5: 97 percent / imidazole / dimethylformamide / 3 h / Ambient temperature
6: 1.) LiOH, 2.) DIBAL / 1.) THF/MeOH, 0 deg C -> RT, 2 h, 2.) CH2Cl2, -78 deg C, 10 min
7: 81 percent / DEAD, Ph3P / toluene / 6 h / 45 °C
8: 94 percent / TBAF / tetrahydrofuran / 3 h / Ambient temperature
9: 87 percent / DEAD, Ph3P / dimethylformamide / 0.67 h / 145 °C
10: 95 percent / H2 / 10 percent Pd/C / ethyl acetate / 3 h / Ambient temperature
With
pyridine; 1H-imidazole; lithium hydroxide; potassium dioxotetrahydroxoosmate(VI); copper(I) bromide dimethylsulfide complex; tetrabutyl ammonium fluoride; hydrogen; diisobutylaluminium hydride; potassium carbonate; 1,4-bis(9-O-dihydroquinidine)phthalazine; triphenylphosphine; potassium hexacyanoferrate(III); diethylazodicarboxylate;
palladium on activated charcoal;
In
tetrahydrofuran; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;
DOI:10.1016/0040-4039(95)01987-S
