Technology Process of 3(2H)-furanone, 5-hydroxy-4-[(2S)-2-[(1S,2S,6R)-2-[(1E)-3-hydroxy-2-[(2R,3R)-tetrahydro-3-methyl-6-[(1E,3S)-3-[(2R,3S,5R)-tetrahydro-5-[(1S)-1-methoxyethyl]-3-methyl-2-furanyl]-1-butenyl]-2H-pyran-2-yl]-1-propenyl]-6-methylcyclohexyl]-1-oxopropyl]-, monos
There total 29 articles about 3(2H)-furanone, 5-hydroxy-4-[(2S)-2-[(1S,2S,6R)-2-[(1E)-3-hydroxy-2-[(2R,3R)-tetrahydro-3-methyl-6-[(1E,3S)-3-[(2R,3S,5R)-tetrahydro-5-[(1S)-1-methoxyethyl]-3-methyl-2-furanyl]-1-butenyl]-2H-pyran-2-yl]-1-propenyl]-6-methylcyclohexyl]-1-oxopropyl]-, monos which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 8 steps
1: 1.) LDA / 1.) THF, -100 deg C, 2.) -95 deg C, 30 min
2: pyridine, DMAP
3: DBU / Ambient temperature
4: 34 percent / acetone / 0 °C / Irradiation
5: (i-Bu)2AlH (DIBALH) / toluene
6: imidazole
7: 80 percent / ZrCl4 / CH2Cl2 / 0.25 h / 0 °C
8: 1.) n-Bu4NF (TBAF), 2.) HF / 1.) THF, 2.) CH3CN
With
pyridine; 1H-imidazole; dmap; hydrogen fluoride; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium diisopropyl amide;
zirconium(IV) chloride;
In
dichloromethane; acetone; toluene;
DOI:10.1016/S0040-4039(00)60377-5
- Guidance literature:
-
Multi-step reaction with 22 steps
1: toluene / -75 °C
2: n-Bu4NF (TBAF) / tetrahydrofuran / r.t. to 50 deg C
3: 83 percent / NaH
4: O3
5: NaBH4
6: Bu3P, pyridine
7: mcpba / CH2Cl2
8: 1.) n-BuLi / 1.) THF
9: NaN(TMS)2
10: AIBN / toluene
11: (i-Bu)2AlH (DIBALH)
12: DMSO, (COCl)2, Et3N / CH2Cl2
13: NaClO2
15: 1.) LDA / 1.) THF, -100 deg C, 2.) -95 deg C, 30 min
16: pyridine, DMAP
17: DBU / Ambient temperature
18: 34 percent / acetone / 0 °C / Irradiation
19: (i-Bu)2AlH (DIBALH) / toluene
20: imidazole
21: 80 percent / ZrCl4 / CH2Cl2 / 0.25 h / 0 °C
22: 1.) n-Bu4NF (TBAF), 2.) HF / 1.) THF, 2.) CH3CN
With
pyridine; 1H-imidazole; dmap; sodium chlorite; sodium tetrahydroborate; n-butyllithium; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); tributylphosphine; hydrogen fluoride; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; sodium hydride; diisobutylaluminium hydride; ozone; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide;
zirconium(IV) chloride;
In
tetrahydrofuran; dichloromethane; acetone; toluene;
DOI:10.1016/S0040-4039(00)60377-5
- Guidance literature:
-
Multi-step reaction with 15 steps
1: 1.) n-BuLi / 1.) THF
2: NaN(TMS)2
3: AIBN / toluene
4: (i-Bu)2AlH (DIBALH)
5: DMSO, (COCl)2, Et3N / CH2Cl2
6: NaClO2
8: 1.) LDA / 1.) THF, -100 deg C, 2.) -95 deg C, 30 min
9: pyridine, DMAP
10: DBU / Ambient temperature
11: 34 percent / acetone / 0 °C / Irradiation
12: (i-Bu)2AlH (DIBALH) / toluene
13: imidazole
14: 80 percent / ZrCl4 / CH2Cl2 / 0.25 h / 0 °C
15: 1.) n-Bu4NF (TBAF), 2.) HF / 1.) THF, 2.) CH3CN
With
pyridine; 1H-imidazole; dmap; sodium chlorite; n-butyllithium; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); hydrogen fluoride; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; diisobutylaluminium hydride; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium diisopropyl amide;
zirconium(IV) chloride;
In
dichloromethane; acetone; toluene;
DOI:10.1016/S0040-4039(00)60377-5