Technology Process of 1-[(1S,2R,3R,4S,5S)-4,5-Bis-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-bicyclo[3.1.0]hex-2-yl]-3-((Z)-3-ethoxy-acryloyl)-isourea
There total 13 articles about 1-[(1S,2R,3R,4S,5S)-4,5-Bis-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-bicyclo[3.1.0]hex-2-yl]-3-((Z)-3-ethoxy-acryloyl)-isourea which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 12 steps
1: 90 percent / Et2Zn / tetrahydrofuran / Ambient temperature
2: 57 percent / p-TsOH / 2 h / 50 °C
3: 100 percent / TPAP, NMP, 4A MS / CH2Cl2 / Ambient temperature
4: 90 percent / n-BuLi / tetrahydrofuran / 0.5 h / 0 °C
5: BH3*THF, NaBO3 / H2O
6: NaH
7: 100 percent / HCl / methanol; tetrahydrofuran / 5 h / 50 °C
8: 100 percent / SOCl2 / triethylamine / 0.05 h / 0 °C
9: NaN3 / dimethylformamide
11: Lindlar catalyst
With
1-methyl-pyrrolidin-2-one; hydrogenchloride; sodium perborate; Lindlar's catalyst; n-butyllithium; thionyl chloride; sodium azide; tetrapropylammonium perruthennate; borane-THF; diethylzinc; sodium hydride; toluene-4-sulfonic acid;
In
tetrahydrofuran; methanol; dichloromethane; water; triethylamine; N,N-dimethyl-formamide;
DOI:10.1080/07328319708006132
- Guidance literature:
-
Multi-step reaction with 13 steps
1: 98 percent / CeCl3*7H2O / methanol / 0 °C
2: 90 percent / Et2Zn / tetrahydrofuran / Ambient temperature
3: 57 percent / p-TsOH / 2 h / 50 °C
4: 100 percent / TPAP, NMP, 4A MS / CH2Cl2 / Ambient temperature
5: 90 percent / n-BuLi / tetrahydrofuran / 0.5 h / 0 °C
6: BH3*THF, NaBO3 / H2O
7: NaH
8: 100 percent / HCl / methanol; tetrahydrofuran / 5 h / 50 °C
9: 100 percent / SOCl2 / triethylamine / 0.05 h / 0 °C
10: NaN3 / dimethylformamide
12: Lindlar catalyst
With
1-methyl-pyrrolidin-2-one; hydrogenchloride; sodium perborate; Lindlar's catalyst; n-butyllithium; thionyl chloride; sodium azide; cerium(III) chloride; tetrapropylammonium perruthennate; borane-THF; diethylzinc; sodium hydride; toluene-4-sulfonic acid;
In
tetrahydrofuran; methanol; dichloromethane; water; triethylamine; N,N-dimethyl-formamide;
DOI:10.1080/07328319708006132
- Guidance literature:
-
Multi-step reaction with 11 steps
1: 57 percent / p-TsOH / 2 h / 50 °C
2: 100 percent / TPAP, NMP, 4A MS / CH2Cl2 / Ambient temperature
3: 90 percent / n-BuLi / tetrahydrofuran / 0.5 h / 0 °C
4: BH3*THF, NaBO3 / H2O
5: NaH
6: 100 percent / HCl / methanol; tetrahydrofuran / 5 h / 50 °C
7: 100 percent / SOCl2 / triethylamine / 0.05 h / 0 °C
8: NaN3 / dimethylformamide
10: Lindlar catalyst
With
1-methyl-pyrrolidin-2-one; hydrogenchloride; sodium perborate; Lindlar's catalyst; n-butyllithium; thionyl chloride; sodium azide; tetrapropylammonium perruthennate; borane-THF; sodium hydride; toluene-4-sulfonic acid;
In
tetrahydrofuran; methanol; dichloromethane; water; triethylamine; N,N-dimethyl-formamide;
DOI:10.1080/07328319708006132