Technology Process of methyl (4S,5R,Z)-3-N-benzyloxycarbonyl-5,6-isopropylidene-2-hexenoate
There total 10 articles about methyl (4S,5R,Z)-3-N-benzyloxycarbonyl-5,6-isopropylidene-2-hexenoate which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
bis-(2,2,2-trifluoroethyl)(methoxycarbonylmethyl)phosphonate;
With
18-crown-6 ether; potassium hexamethylsilazane;
In
tetrahydrofuran;
at -65 ℃;
for 0.333333h;
[(R)-1-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2-oxo-ethyl]-carbamic acid benzyl ester;
In
tetrahydrofuran;
at -78 ℃;
for 0.75h;
DOI:10.1016/S0957-4166(99)00316-X
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: imidazole / tetrahydrofuran / 3 h / -5 °C
2.1: Et3N / CH2Cl2 / 1 h / 20 °C
3.1: NaN3 / dimethylformamide / 10 h / 95 °C
4.1: H2 / 10 percent Pd/C / ethanol / 6 h
5.1: Et3N / tetrahydrofuran
6.1: tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C
7.1: oxalyl chloride, DMSO; N,N-diisopropylethyl amine / CH2Cl2 / 0.42 h / -63 °C
8.1: 18-crown-6; KN(TMS)2 / tetrahydrofuran / 0.33 h / -65 °C
8.2: 93 percent / tetrahydrofuran / 0.75 h / -78 °C
With
1H-imidazole; sodium azide; oxalyl dichloride; 18-crown-6 ether; tetrabutyl ammonium fluoride; hydrogen; potassium hexamethylsilazane; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine;
palladium on activated charcoal;
In
tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide;
1.1: silylation / 2.1: mesylation / 3.1: Substitution / 4.1: Hydrogenation / 5.1: carbobenzoxylation / 6.1: desilylation / 7.1: Oxidation / 8.1: Metallation / 8.2: Condensation;
DOI:10.1016/S0957-4166(99)00316-X
- Guidance literature:
-
Multi-step reaction with 10 steps
1.1: 83 percent / triphenylphosphine; diisopropyl diazodicarboxylate / tetrahydrofuran / 24 h / 20 °C
2.1: 92 percent / LiAlH4 / tetrahydrofuran / 3 h / Heating
3.1: imidazole / tetrahydrofuran / 3 h / -5 °C
4.1: Et3N / CH2Cl2 / 1 h / 20 °C
5.1: NaN3 / dimethylformamide / 10 h / 95 °C
6.1: H2 / 10 percent Pd/C / ethanol / 6 h
7.1: Et3N / tetrahydrofuran
8.1: tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C
9.1: oxalyl chloride, DMSO; N,N-diisopropylethyl amine / CH2Cl2 / 0.42 h / -63 °C
10.1: 18-crown-6; KN(TMS)2 / tetrahydrofuran / 0.33 h / -65 °C
10.2: 93 percent / tetrahydrofuran / 0.75 h / -78 °C
With
1H-imidazole; lithium aluminium tetrahydride; sodium azide; oxalyl dichloride; 18-crown-6 ether; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; hydrogen; potassium hexamethylsilazane; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine;
palladium on activated charcoal;
In
tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide;
1.1: Esterification / 2.1: Reduction / 3.1: silylation / 4.1: mesylation / 5.1: Substitution / 6.1: Hydrogenation / 7.1: carbobenzoxylation / 8.1: desilylation / 9.1: Oxidation / 10.1: Metallation / 10.2: Condensation;
DOI:10.1016/S0957-4166(99)00316-X
