Technology Process of (E)-(7S,9R,10S)-9-(tert-Butyl-dimethyl-silanyloxy)-4-methoxy-7-[(E)-4-(4-methoxy-benzyloxy)-but-2-enyl]-10-methyl-7,8,9,10,11,14-hexahydro-6-oxa-benzocyclododecen-5-one
There total 13 articles about (E)-(7S,9R,10S)-9-(tert-Butyl-dimethyl-silanyloxy)-4-methoxy-7-[(E)-4-(4-methoxy-benzyloxy)-but-2-enyl]-10-methyl-7,8,9,10,11,14-hexahydro-6-oxa-benzocyclododecen-5-one which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 9 steps
1.1: 97 percent / 2,6-lutidine / CH2Cl2 / -78 - 20 °C
2.1: 9-BBN / tetrahydrofuran / 3 h / Heating
2.2: 89 percent / NaOH; H2O2 / tetrahydrofuran; H2O / 0 - 20 °C
3.1: 96 percent / dimethyl sulfoxide; oxalyl chloride; triethylamine / CH2Cl2 / -78 - 20 °C
4.1: NaHMDS / tetrahydrofuran / 0.5 h / 0 °C
4.2: 81 percent / tetrahydrofuran / -78 - 20 °C
5.1: 90 percent / aqueous trifluoroacetic acid / CH2Cl2 / 0.5 h / 20 °C
6.1: 81 percent / NaH; tosylimidazole / tetrahydrofuran / -78 - 0 °C
7.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C
7.2: magnesium; 1,2-dibromoethane / various solvents / 0.75 h / -78 °C
7.3: 94 percent / CuI / various solvents / -78 - 0 °C
8.1: 84 percent / triphenylphosphine; diethyl azodicarboxylate / benzene / 24 h
9.1: (Cy3P)2Cl2Ru=CHPh / CH2Cl2 / 0.67 h / 20 °C
With
2,6-dimethylpyridine; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; oxalyl dichloride; sodium hexamethyldisilazane; sodium hydride; dimethyl sulfoxide; triethylamine; triphenylphosphine; N-tosylimidazole; trifluoroacetic acid; diethylazodicarboxylate;
Grubbs catalyst first generation;
In
tetrahydrofuran; hexane; dichloromethane; benzene;
3.1: Swern oxidation / 4.2: Wittig methylenation / 6.1: Kishi epoxidation / 8.1: Mitsunobu esterification / 9.1: ring closing metathesis;
DOI:10.1016/S0040-4020(02)00657-9
- Guidance literature:
-
Multi-step reaction with 4 steps
1: 65 percent / I2 / tetrahydrofuran; H2O / 24 h / 20 °C
2: 73 percent / zinc; acetic acid / 24 h / 90 °C
3: 84 percent / triphenylphosphine; diethyl azodicarboxylate / benzene / 24 h
4: (Cy3P)2Cl2Ru=CHPh / CH2Cl2 / 0.67 h / 20 °C
With
iodine; acetic acid; triphenylphosphine; zinc; diethylazodicarboxylate;
Grubbs catalyst first generation;
In
tetrahydrofuran; dichloromethane; water; benzene;
3: Mitsunobu esterification / 4: ring closing metathesis;
DOI:10.1016/S0040-4020(02)00657-9
- Guidance literature:
-
Multi-step reaction with 2 steps
1: 84 percent / triphenylphosphine; diethyl azodicarboxylate / benzene / 24 h
2: (Cy3P)2Cl2Ru=CHPh / CH2Cl2 / 0.67 h / 20 °C
With
triphenylphosphine; diethylazodicarboxylate;
Grubbs catalyst first generation;
In
dichloromethane; benzene;
1: Mitsunobu esterification / 2: ring closing metathesis;
DOI:10.1016/S0040-4020(02)00657-9
