Technology Process of O-(t-Butyldimethylsilyl)-(-)-(2R,3R,6S,8S)-homononactyl-(+)-(2S,3S.6R,8R)-homononactyl-(-)-(2R,3R,6S,8S)-homononactyl-(+)-(2S,3S,6R,8R)-homononactinsaeure-benzylester
There total 20 articles about O-(t-Butyldimethylsilyl)-(-)-(2R,3R,6S,8S)-homononactyl-(+)-(2S,3S.6R,8R)-homononactyl-(-)-(2R,3R,6S,8S)-homononactyl-(+)-(2S,3S,6R,8R)-homononactinsaeure-benzylester which
guide to synthetic route it.
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synthetic route:
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105238-82-2,111001-55-9
O-(t-Butyldimethylsilyl)-(-)-(2R,3R,6S,8S)-homononactyl-(+)-(2S,3S.6R,8R)-homononactyl-(-)-(2R,3R,6S,8S)-homononactyl-(+)-(2S,3S,6R,8R)-homononactinsaeure-benzylester
- Guidance literature:
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Multi-step reaction with 12 steps
1: 1.) m-tolyl-lithium / 2.) THF, 5 deg C, 4 h, to room temp.
2: 0.5 h
3: 90 percent / TPP, H2 / 2 / 24 h / 70 °C / 76000 Torr
4: NaClO2, H2N-SO3H, Na2HPO4 / dioxane; H2O / 0.5 h / Ambient temperature
5: KOH / methanol / 0.5 h / Ambient temperature
6: diethyl ether / 0.03 h / Ambient temperature
7: H2 / 5percent Rh/Al2O3 / methanol / 1.5 h / 2280 Torr / Ambient temperature
8: KOH / methanol / 0.5 h / Ambient temperature
9: 1.) KHCO3 / 1.) H2O, 2.) DMF, 50 deg C, 1 h
10: 94 percent / Et3N, DMAP / CH2Cl2 / 1 h / 0 °C
11: 1.) KHCO3 / 1.) H2O, 2.) DMSO, 50 deg C, 16 h
12: 4-pyrrolidinopyridine / CH2Cl2 / 2 h / Ambient temperature
With
dmap; potassium hydroxide; sodium chlorite; disodium hydrogenphosphate; aminosulfonic acid; hydrogen; thiamine diphosphate; m-tolyllithium; potassium hydrogencarbonate; 4-pyrrolidin-1-ylpyridine; triethylamine;
Rh/Al2O3; chloro(1,5-cyclooctadiene)rhodium(I) dimer;
In
1,4-dioxane; methanol; diethyl ether; dichloromethane; water;
DOI:10.1039/c39860000996
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105238-82-2,111001-55-9
O-(t-Butyldimethylsilyl)-(-)-(2R,3R,6S,8S)-homononactyl-(+)-(2S,3S.6R,8R)-homononactyl-(-)-(2R,3R,6S,8S)-homononactyl-(+)-(2S,3S,6R,8R)-homononactinsaeure-benzylester
- Guidance literature:
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Multi-step reaction with 7 steps
1: diethyl ether / 0.03 h / Ambient temperature
2: H2 / 5percent Rh/Al2O3 / methanol / 1.5 h / 2280 Torr / Ambient temperature
3: KOH / methanol / 0.5 h / Ambient temperature
4: 1.) KHCO3 / 1.) H2O, 2.) DMF, 50 deg C, 1 h
5: 94 percent / Et3N, DMAP / CH2Cl2 / 1 h / 0 °C
6: 1.) KHCO3 / 1.) H2O, 2.) DMSO, 50 deg C, 16 h
7: 4-pyrrolidinopyridine / CH2Cl2 / 2 h / Ambient temperature
With
dmap; potassium hydroxide; hydrogen; potassium hydrogencarbonate; 4-pyrrolidin-1-ylpyridine; triethylamine;
Rh/Al2O3;
In
methanol; diethyl ether; dichloromethane;
DOI:10.1039/c39860000996
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105238-82-2,111001-55-9
O-(t-Butyldimethylsilyl)-(-)-(2R,3R,6S,8S)-homononactyl-(+)-(2S,3S.6R,8R)-homononactyl-(-)-(2R,3R,6S,8S)-homononactyl-(+)-(2S,3S,6R,8R)-homononactinsaeure-benzylester
- Guidance literature:
-
Multi-step reaction with 10 steps
1: 90 percent / TPP, H2 / 2 / 24 h / 70 °C / 76000 Torr
2: NaClO2, H2N-SO3H, Na2HPO4 / dioxane; H2O / 0.5 h / Ambient temperature
3: KOH / methanol / 0.5 h / Ambient temperature
4: diethyl ether / 0.03 h / Ambient temperature
5: H2 / 5percent Rh/Al2O3 / methanol / 1.5 h / 2280 Torr / Ambient temperature
6: KOH / methanol / 0.5 h / Ambient temperature
7: 1.) KHCO3 / 1.) H2O, 2.) DMF, 50 deg C, 1 h
8: 94 percent / Et3N, DMAP / CH2Cl2 / 1 h / 0 °C
9: 1.) KHCO3 / 1.) H2O, 2.) DMSO, 50 deg C, 16 h
10: 4-pyrrolidinopyridine / CH2Cl2 / 2 h / Ambient temperature
With
dmap; potassium hydroxide; sodium chlorite; disodium hydrogenphosphate; aminosulfonic acid; hydrogen; thiamine diphosphate; potassium hydrogencarbonate; 4-pyrrolidin-1-ylpyridine; triethylamine;
Rh/Al2O3; chloro(1,5-cyclooctadiene)rhodium(I) dimer;
In
1,4-dioxane; methanol; diethyl ether; dichloromethane; water;
DOI:10.1039/c39860000996
