solanesol
Conditions | Yield |
---|---|
With lithium; ethylamine In diethyl ether at -78℃; | 50% |
(2E,6E)-3,7,11-trimethyl-1-(p-tolylsulfonyl)dodeca-2,6,10-triene
(2E,6E,10E)-1-Benzyloxy-3,7,11-trimethyldodeca-2,6,10-trien-12-ol
(2E,6E,10E)-2,6,10-trimethyl-12-(toluene-4-sulfonyl)-dodeca-2,6,10-trien-1-ol
solanesol
Conditions | Yield |
---|---|
Multistep reaction; |
3,7-dimethyl-2E,6-octadien-1-yl acetate
solanesol
Conditions | Yield |
---|---|
Multi-step reaction with 14 steps 1: 44 percent / SeO2 / aq. ethanol / 9 h / Heating 2: 72 percent / NaBH4 / methanol / 5 h / -10 °C 3: 94 percent / PBr3, pyridine / diethyl ether / 6 h / 0 °C 4: 1.) n-BuLi / 1.) THF, HMPA, hexane, -78 deg C, 1.5 h, 2.) 6 h 5: 5percent sodium amalgam, disodium hydrogen phosphate / methanol / 2 h / 0 °C 6: 91 percent / PBr3, pyridine / diethyl ether / 6 h / -5 °C 7: 78 percent / dimethylformamide / 24 h / Ambient temperature 8: 1.) n-BuLi, 3.) H2O, KOH 9: 63 percent / Li, ethylamine / diethyl ether / 1 h / -78 °C 10: 1.) PBr3, pyridine / 1.) ether, 2.) DMF, ambient temperature 11: 1.) n-BuLi, 3.) H2O, KOH 12: 70 percent / Li, ethylamine / diethyl ether 13: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C 14: 50 percent / Li, ethylamine / diethyl ether / -78 °C View Scheme | |
Multi-step reaction with 13 steps 1: 44 percent / SeO2 / aq. ethanol / 9 h / Heating 2: 72 percent / NaBH4 / methanol / 5 h / -10 °C 3: 94 percent / PBr3, pyridine / diethyl ether / 6 h / 0 °C 4: 1.) n-BuLi / 1.) THF, HMPA, hexane, -78 deg C, 1.5 h, 2.) 6 h 5: NaOMe / methanol / 2 h / Ambient temperature 7: 1.) n-BuLi, 3.) H2O, KOH 8: 63 percent / Li, ethylamine / diethyl ether / 1 h / -78 °C 9: 1.) PBr3, pyridine / 1.) ether, 2.) DMF, ambient temperature 10: 1.) n-BuLi, 3.) H2O, KOH 11: 70 percent / Li, ethylamine / diethyl ether 12: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C 13: 50 percent / Li, ethylamine / diethyl ether / -78 °C View Scheme | |
Multi-step reaction with 15 steps 1: 44 percent / SeO2 / aq. ethanol / 9 h / Heating 2: 72 percent / NaBH4 / methanol / 5 h / -10 °C 3: 94 percent / PBr3, pyridine / diethyl ether / 6 h / 0 °C 4: 1.) n-BuLi / 1.) THF, HMPA, hexane, -78 deg C, 1.5 h, 2.) 6 h 5: NaOMe / methanol / 2 h / Ambient temperature 6: 264 mg / Li, ethylamine / diethyl ether / 1 h / -78 °C 7: 91 percent / PBr3, pyridine / diethyl ether / 6 h / -5 °C 8: 78 percent / dimethylformamide / 24 h / Ambient temperature 9: 1.) n-BuLi, 3.) H2O, KOH 10: 63 percent / Li, ethylamine / diethyl ether / 1 h / -78 °C 11: 1.) PBr3, pyridine / 1.) ether, 2.) DMF, ambient temperature 12: 1.) n-BuLi, 3.) H2O, KOH 13: 70 percent / Li, ethylamine / diethyl ether 14: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C 15: 50 percent / Li, ethylamine / diethyl ether / -78 °C View Scheme |
2E,6E,10E-geranylgeranyl bromide
solanesol
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1: 78 percent / dimethylformamide / 24 h / Ambient temperature 2: 1.) n-BuLi, 3.) H2O, KOH 3: 63 percent / Li, ethylamine / diethyl ether / 1 h / -78 °C 4: 1.) PBr3, pyridine / 1.) ether, 2.) DMF, ambient temperature 5: 1.) n-BuLi, 3.) H2O, KOH 6: 70 percent / Li, ethylamine / diethyl ether 7: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C 8: 50 percent / Li, ethylamine / diethyl ether / -78 °C View Scheme |
(2E,6E)-8-bromo-3,7-dimethylocta-2,6-dienyl acetate
solanesol
Conditions | Yield |
---|---|
Multi-step reaction with 11 steps 1: 1.) n-BuLi / 1.) THF, HMPA, hexane, -78 deg C, 1.5 h, 2.) 6 h 2: 5percent sodium amalgam, disodium hydrogen phosphate / methanol / 2 h / 0 °C 3: 91 percent / PBr3, pyridine / diethyl ether / 6 h / -5 °C 4: 78 percent / dimethylformamide / 24 h / Ambient temperature 5: 1.) n-BuLi, 3.) H2O, KOH 6: 63 percent / Li, ethylamine / diethyl ether / 1 h / -78 °C 7: 1.) PBr3, pyridine / 1.) ether, 2.) DMF, ambient temperature 8: 1.) n-BuLi, 3.) H2O, KOH 9: 70 percent / Li, ethylamine / diethyl ether 10: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C 11: 50 percent / Li, ethylamine / diethyl ether / -78 °C View Scheme | |
Multi-step reaction with 10 steps 1: 1.) n-BuLi / 1.) THF, HMPA, hexane, -78 deg C, 1.5 h, 2.) 6 h 2: NaOMe / methanol / 2 h / Ambient temperature 4: 1.) n-BuLi, 3.) H2O, KOH 5: 63 percent / Li, ethylamine / diethyl ether / 1 h / -78 °C 6: 1.) PBr3, pyridine / 1.) ether, 2.) DMF, ambient temperature 7: 1.) n-BuLi, 3.) H2O, KOH 8: 70 percent / Li, ethylamine / diethyl ether 9: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C 10: 50 percent / Li, ethylamine / diethyl ether / -78 °C View Scheme | |
Multi-step reaction with 12 steps 1: 1.) n-BuLi / 1.) THF, HMPA, hexane, -78 deg C, 1.5 h, 2.) 6 h 2: NaOMe / methanol / 2 h / Ambient temperature 3: 264 mg / Li, ethylamine / diethyl ether / 1 h / -78 °C 4: 91 percent / PBr3, pyridine / diethyl ether / 6 h / -5 °C 5: 78 percent / dimethylformamide / 24 h / Ambient temperature 6: 1.) n-BuLi, 3.) H2O, KOH 7: 63 percent / Li, ethylamine / diethyl ether / 1 h / -78 °C 8: 1.) PBr3, pyridine / 1.) ether, 2.) DMF, ambient temperature 9: 1.) n-BuLi, 3.) H2O, KOH 10: 70 percent / Li, ethylamine / diethyl ether 11: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C 12: 50 percent / Li, ethylamine / diethyl ether / -78 °C View Scheme | |
Multi-step reaction with 7 steps 1: 1.) n-BuLi, 3.) H2O, KOH 2: 63 percent / Li, ethylamine / diethyl ether / 1 h / -78 °C 3: 1.) PBr3, pyridine / 1.) ether, 2.) DMF, ambient temperature 4: 1.) n-BuLi, 3.) H2O, KOH 5: 70 percent / Li, ethylamine / diethyl ether 6: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C 7: 50 percent / Li, ethylamine / diethyl ether / -78 °C View Scheme | |
Multi-step reaction with 4 steps 1: 1.) n-BuLi, 3.) H2O, KOH 2: 70 percent / Li, ethylamine / diethyl ether 3: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C 4: 50 percent / Li, ethylamine / diethyl ether / -78 °C View Scheme |
8-hydroxygeranyl acetate
solanesol
Conditions | Yield |
---|---|
Multi-step reaction with 12 steps 1: 94 percent / PBr3, pyridine / diethyl ether / 6 h / 0 °C 2: 1.) n-BuLi / 1.) THF, HMPA, hexane, -78 deg C, 1.5 h, 2.) 6 h 3: 5percent sodium amalgam, disodium hydrogen phosphate / methanol / 2 h / 0 °C 4: 91 percent / PBr3, pyridine / diethyl ether / 6 h / -5 °C 5: 78 percent / dimethylformamide / 24 h / Ambient temperature 6: 1.) n-BuLi, 3.) H2O, KOH 7: 63 percent / Li, ethylamine / diethyl ether / 1 h / -78 °C 8: 1.) PBr3, pyridine / 1.) ether, 2.) DMF, ambient temperature 9: 1.) n-BuLi, 3.) H2O, KOH 10: 70 percent / Li, ethylamine / diethyl ether 11: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C 12: 50 percent / Li, ethylamine / diethyl ether / -78 °C View Scheme | |
Multi-step reaction with 11 steps 1: 94 percent / PBr3, pyridine / diethyl ether / 6 h / 0 °C 2: 1.) n-BuLi / 1.) THF, HMPA, hexane, -78 deg C, 1.5 h, 2.) 6 h 3: NaOMe / methanol / 2 h / Ambient temperature 5: 1.) n-BuLi, 3.) H2O, KOH 6: 63 percent / Li, ethylamine / diethyl ether / 1 h / -78 °C 7: 1.) PBr3, pyridine / 1.) ether, 2.) DMF, ambient temperature 8: 1.) n-BuLi, 3.) H2O, KOH 9: 70 percent / Li, ethylamine / diethyl ether 10: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C 11: 50 percent / Li, ethylamine / diethyl ether / -78 °C View Scheme | |
Multi-step reaction with 13 steps 1: 94 percent / PBr3, pyridine / diethyl ether / 6 h / 0 °C 2: 1.) n-BuLi / 1.) THF, HMPA, hexane, -78 deg C, 1.5 h, 2.) 6 h 3: NaOMe / methanol / 2 h / Ambient temperature 4: 264 mg / Li, ethylamine / diethyl ether / 1 h / -78 °C 5: 91 percent / PBr3, pyridine / diethyl ether / 6 h / -5 °C 6: 78 percent / dimethylformamide / 24 h / Ambient temperature 7: 1.) n-BuLi, 3.) H2O, KOH 8: 63 percent / Li, ethylamine / diethyl ether / 1 h / -78 °C 9: 1.) PBr3, pyridine / 1.) ether, 2.) DMF, ambient temperature 10: 1.) n-BuLi, 3.) H2O, KOH 11: 70 percent / Li, ethylamine / diethyl ether 12: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C 13: 50 percent / Li, ethylamine / diethyl ether / -78 °C View Scheme | |
Multi-step reaction with 8 steps 1: 94 percent / PBr3, pyridine / diethyl ether / 6 h / 0 °C 2: 1.) n-BuLi, 3.) H2O, KOH 3: 63 percent / Li, ethylamine / diethyl ether / 1 h / -78 °C 4: 1.) PBr3, pyridine / 1.) ether, 2.) DMF, ambient temperature 5: 1.) n-BuLi, 3.) H2O, KOH 6: 70 percent / Li, ethylamine / diethyl ether 7: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C 8: 50 percent / Li, ethylamine / diethyl ether / -78 °C View Scheme | |
Multi-step reaction with 5 steps 1: 94 percent / PBr3, pyridine / diethyl ether / 6 h / 0 °C 2: 1.) n-BuLi, 3.) H2O, KOH 3: 70 percent / Li, ethylamine / diethyl ether 4: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C 5: 50 percent / Li, ethylamine / diethyl ether / -78 °C View Scheme |
(2E,6E)-3,7-dimethyl-8-oxoocta-2,6-dien-1-yl acetate
solanesol
Conditions | Yield |
---|---|
Multi-step reaction with 13 steps 1: 72 percent / NaBH4 / methanol / 5 h / -10 °C 2: 94 percent / PBr3, pyridine / diethyl ether / 6 h / 0 °C 3: 1.) n-BuLi / 1.) THF, HMPA, hexane, -78 deg C, 1.5 h, 2.) 6 h 4: 5percent sodium amalgam, disodium hydrogen phosphate / methanol / 2 h / 0 °C 5: 91 percent / PBr3, pyridine / diethyl ether / 6 h / -5 °C 6: 78 percent / dimethylformamide / 24 h / Ambient temperature 7: 1.) n-BuLi, 3.) H2O, KOH 8: 63 percent / Li, ethylamine / diethyl ether / 1 h / -78 °C 9: 1.) PBr3, pyridine / 1.) ether, 2.) DMF, ambient temperature 10: 1.) n-BuLi, 3.) H2O, KOH 11: 70 percent / Li, ethylamine / diethyl ether 12: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C 13: 50 percent / Li, ethylamine / diethyl ether / -78 °C View Scheme | |
Multi-step reaction with 12 steps 1: 72 percent / NaBH4 / methanol / 5 h / -10 °C 2: 94 percent / PBr3, pyridine / diethyl ether / 6 h / 0 °C 3: 1.) n-BuLi / 1.) THF, HMPA, hexane, -78 deg C, 1.5 h, 2.) 6 h 4: NaOMe / methanol / 2 h / Ambient temperature 6: 1.) n-BuLi, 3.) H2O, KOH 7: 63 percent / Li, ethylamine / diethyl ether / 1 h / -78 °C 8: 1.) PBr3, pyridine / 1.) ether, 2.) DMF, ambient temperature 9: 1.) n-BuLi, 3.) H2O, KOH 10: 70 percent / Li, ethylamine / diethyl ether 11: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C 12: 50 percent / Li, ethylamine / diethyl ether / -78 °C View Scheme | |
Multi-step reaction with 14 steps 1: 72 percent / NaBH4 / methanol / 5 h / -10 °C 2: 94 percent / PBr3, pyridine / diethyl ether / 6 h / 0 °C 3: 1.) n-BuLi / 1.) THF, HMPA, hexane, -78 deg C, 1.5 h, 2.) 6 h 4: NaOMe / methanol / 2 h / Ambient temperature 5: 264 mg / Li, ethylamine / diethyl ether / 1 h / -78 °C 6: 91 percent / PBr3, pyridine / diethyl ether / 6 h / -5 °C 7: 78 percent / dimethylformamide / 24 h / Ambient temperature 8: 1.) n-BuLi, 3.) H2O, KOH 9: 63 percent / Li, ethylamine / diethyl ether / 1 h / -78 °C 10: 1.) PBr3, pyridine / 1.) ether, 2.) DMF, ambient temperature 11: 1.) n-BuLi, 3.) H2O, KOH 12: 70 percent / Li, ethylamine / diethyl ether 13: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C 14: 50 percent / Li, ethylamine / diethyl ether / -78 °C View Scheme |
Geranylgeraniol
solanesol
Conditions | Yield |
---|---|
Multi-step reaction with 9 steps 1: 91 percent / PBr3, pyridine / diethyl ether / 6 h / -5 °C 2: 78 percent / dimethylformamide / 24 h / Ambient temperature 3: 1.) n-BuLi, 3.) H2O, KOH 4: 63 percent / Li, ethylamine / diethyl ether / 1 h / -78 °C 5: 1.) PBr3, pyridine / 1.) ether, 2.) DMF, ambient temperature 6: 1.) n-BuLi, 3.) H2O, KOH 7: 70 percent / Li, ethylamine / diethyl ether 8: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C 9: 50 percent / Li, ethylamine / diethyl ether / -78 °C View Scheme |
3,7-dimethyl-1-(p-toluenesulfonyl)-2(E),6-octadiene
solanesol
Conditions | Yield |
---|---|
Multi-step reaction with 11 steps 1: 1.) n-BuLi / 1.) THF, HMPA, hexane, -78 deg C, 1.5 h, 2.) 6 h 2: 5percent sodium amalgam, disodium hydrogen phosphate / methanol / 2 h / 0 °C 3: 91 percent / PBr3, pyridine / diethyl ether / 6 h / -5 °C 4: 78 percent / dimethylformamide / 24 h / Ambient temperature 5: 1.) n-BuLi, 3.) H2O, KOH 6: 63 percent / Li, ethylamine / diethyl ether / 1 h / -78 °C 7: 1.) PBr3, pyridine / 1.) ether, 2.) DMF, ambient temperature 8: 1.) n-BuLi, 3.) H2O, KOH 9: 70 percent / Li, ethylamine / diethyl ether 10: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C 11: 50 percent / Li, ethylamine / diethyl ether / -78 °C View Scheme | |
Multi-step reaction with 10 steps 1: 1.) n-BuLi / 1.) THF, HMPA, hexane, -78 deg C, 1.5 h, 2.) 6 h 2: NaOMe / methanol / 2 h / Ambient temperature 4: 1.) n-BuLi, 3.) H2O, KOH 5: 63 percent / Li, ethylamine / diethyl ether / 1 h / -78 °C 6: 1.) PBr3, pyridine / 1.) ether, 2.) DMF, ambient temperature 7: 1.) n-BuLi, 3.) H2O, KOH 8: 70 percent / Li, ethylamine / diethyl ether 9: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C 10: 50 percent / Li, ethylamine / diethyl ether / -78 °C View Scheme | |
Multi-step reaction with 12 steps 1: 1.) n-BuLi / 1.) THF, HMPA, hexane, -78 deg C, 1.5 h, 2.) 6 h 2: NaOMe / methanol / 2 h / Ambient temperature 3: 264 mg / Li, ethylamine / diethyl ether / 1 h / -78 °C 4: 91 percent / PBr3, pyridine / diethyl ether / 6 h / -5 °C 5: 78 percent / dimethylformamide / 24 h / Ambient temperature 6: 1.) n-BuLi, 3.) H2O, KOH 7: 63 percent / Li, ethylamine / diethyl ether / 1 h / -78 °C 8: 1.) PBr3, pyridine / 1.) ether, 2.) DMF, ambient temperature 9: 1.) n-BuLi, 3.) H2O, KOH 10: 70 percent / Li, ethylamine / diethyl ether 11: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C 12: 50 percent / Li, ethylamine / diethyl ether / -78 °C View Scheme |
(E)-1-O-acetyl-4-chloro-3-methyl-2-buten-1-ol
solanesol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C 2: 50 percent / Li, ethylamine / diethyl ether / -78 °C View Scheme |
(E,E,E,E,E,E,E)-3,7,11,15,19,23,27,31-octamethyldotriaconta-2,6,10,14,18,22,26,30-octaen-1-ol
solanesol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C 2: 50 percent / Li, ethylamine / diethyl ether / -78 °C View Scheme |
(2E,6E,10E,14E,18E)-3,7,11,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaen-1-ol
solanesol
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 1.) PBr3, pyridine / 1.) ether, 2.) DMF, ambient temperature 2: 1.) n-BuLi, 3.) H2O, KOH 3: 70 percent / Li, ethylamine / diethyl ether 4: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C 5: 50 percent / Li, ethylamine / diethyl ether / -78 °C View Scheme |
1-methyl-4-{[(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]sulfonyl}benzene
solanesol
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: 1.) n-BuLi, 3.) H2O, KOH 2: 63 percent / Li, ethylamine / diethyl ether / 1 h / -78 °C 3: 1.) PBr3, pyridine / 1.) ether, 2.) DMF, ambient temperature 4: 1.) n-BuLi, 3.) H2O, KOH 5: 70 percent / Li, ethylamine / diethyl ether 6: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C 7: 50 percent / Li, ethylamine / diethyl ether / -78 °C View Scheme |
(2E,6E,10E)-3,7,11,15-tetramethyl-9-p-tolylsulphonylhexadeca-2,6,10,14-tetraen-1-ol
solanesol
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 2: 1.) n-BuLi, 3.) H2O, KOH 3: 63 percent / Li, ethylamine / diethyl ether / 1 h / -78 °C 4: 1.) PBr3, pyridine / 1.) ether, 2.) DMF, ambient temperature 5: 1.) n-BuLi, 3.) H2O, KOH 6: 70 percent / Li, ethylamine / diethyl ether 7: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C 8: 50 percent / Li, ethylamine / diethyl ether / -78 °C View Scheme | |
Multi-step reaction with 10 steps 1: 264 mg / Li, ethylamine / diethyl ether / 1 h / -78 °C 2: 91 percent / PBr3, pyridine / diethyl ether / 6 h / -5 °C 3: 78 percent / dimethylformamide / 24 h / Ambient temperature 4: 1.) n-BuLi, 3.) H2O, KOH 5: 63 percent / Li, ethylamine / diethyl ether / 1 h / -78 °C 6: 1.) PBr3, pyridine / 1.) ether, 2.) DMF, ambient temperature 7: 1.) n-BuLi, 3.) H2O, KOH 8: 70 percent / Li, ethylamine / diethyl ether 9: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C 10: 50 percent / Li, ethylamine / diethyl ether / -78 °C View Scheme |
(2E,6E,10E)-3,7,11,15-tetramethyl-9-[(4-methylphenyl)sulfonyl]hexadeca-2,6,10,14-tetraen-1-yl acetate
solanesol
Conditions | Yield |
---|---|
Multi-step reaction with 10 steps 1: 5percent sodium amalgam, disodium hydrogen phosphate / methanol / 2 h / 0 °C 2: 91 percent / PBr3, pyridine / diethyl ether / 6 h / -5 °C 3: 78 percent / dimethylformamide / 24 h / Ambient temperature 4: 1.) n-BuLi, 3.) H2O, KOH 5: 63 percent / Li, ethylamine / diethyl ether / 1 h / -78 °C 6: 1.) PBr3, pyridine / 1.) ether, 2.) DMF, ambient temperature 7: 1.) n-BuLi, 3.) H2O, KOH 8: 70 percent / Li, ethylamine / diethyl ether 9: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C 10: 50 percent / Li, ethylamine / diethyl ether / -78 °C View Scheme | |
Multi-step reaction with 9 steps 1: NaOMe / methanol / 2 h / Ambient temperature 3: 1.) n-BuLi, 3.) H2O, KOH 4: 63 percent / Li, ethylamine / diethyl ether / 1 h / -78 °C 5: 1.) PBr3, pyridine / 1.) ether, 2.) DMF, ambient temperature 6: 1.) n-BuLi, 3.) H2O, KOH 7: 70 percent / Li, ethylamine / diethyl ether 8: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C 9: 50 percent / Li, ethylamine / diethyl ether / -78 °C View Scheme | |
Multi-step reaction with 11 steps 1: NaOMe / methanol / 2 h / Ambient temperature 2: 264 mg / Li, ethylamine / diethyl ether / 1 h / -78 °C 3: 91 percent / PBr3, pyridine / diethyl ether / 6 h / -5 °C 4: 78 percent / dimethylformamide / 24 h / Ambient temperature 5: 1.) n-BuLi, 3.) H2O, KOH 6: 63 percent / Li, ethylamine / diethyl ether / 1 h / -78 °C 7: 1.) PBr3, pyridine / 1.) ether, 2.) DMF, ambient temperature 8: 1.) n-BuLi, 3.) H2O, KOH 9: 70 percent / Li, ethylamine / diethyl ether 10: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C 11: 50 percent / Li, ethylamine / diethyl ether / -78 °C View Scheme |
(2E,6E,10E,14E,18E)-3,7,11,15,19,23-hexamethyl-1-p-tolylsulphonyltetracosa-2,6,10,14,18,22-hexaene
solanesol
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 1.) n-BuLi, 3.) H2O, KOH 2: 70 percent / Li, ethylamine / diethyl ether 3: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C 4: 50 percent / Li, ethylamine / diethyl ether / -78 °C View Scheme |
(2E,6E,10E,14E,18E)-3,7,11,15,19,23-hexamethyl-9-p-tolylsulphonyltetracosa-2,6,10,14,18,22-hexaen-1-ol
solanesol
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: 63 percent / Li, ethylamine / diethyl ether / 1 h / -78 °C 2: 1.) PBr3, pyridine / 1.) ether, 2.) DMF, ambient temperature 3: 1.) n-BuLi, 3.) H2O, KOH 4: 70 percent / Li, ethylamine / diethyl ether 5: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C 6: 50 percent / Li, ethylamine / diethyl ether / -78 °C View Scheme |
solanesol
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 70 percent / Li, ethylamine / diethyl ether 2: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C 3: 50 percent / Li, ethylamine / diethyl ether / -78 °C View Scheme |
solanesol
solanesyl bromide
Conditions | Yield |
---|---|
With pyridine; phosphorus tribromide In diethyl ether | 99% |
With phosphorus tribromide; triethylamine In di-isopropyl ether at -10℃; for 2h; Product distribution / selectivity; | 94% |
With phosphorus tribromide In tetrahydrofuran at -10℃; for 2h; Product distribution / selectivity; | 88% |
solanesol
solanesyl chloride
Conditions | Yield |
---|---|
With phosphorus trichloride In N,N-dimethyl-formamide at 20℃; for 1h; | 96.1% |
With N,N-dimethyl-formamide; phosphorus trichloride In tetrahydrofuran at 20℃; for 2h; | 95.1% |
With N,N-dimethyl-formamide; phosphorus trichloride In tetrahydrofuran at 20℃; for 2h; Product distribution / selectivity; | 95.1% |
Conditions | Yield |
---|---|
With pyridine; trichloroacetonitrile at 80℃; for 1h; Microwave irradiation; | 84% |
Conditions | Yield |
---|---|
With pyridine; trichloroacetonitrile at 80℃; for 1h; Microwave irradiation; | 82% |
solanesol
chloroacetyl chloride
chloro-acetic acid 3,7,11,15,19,23,27,31,35-nonamethyl-hexatriaconta-2,6,10,14,18,22,26,30,34-nonaen-1-yl ester
Conditions | Yield |
---|---|
With triethylamine In benzene at 5℃; for 4h; | 80.3% |
succinic acid anhydride
solanesol
succinic acid mono-(3,7,11,15,19,23,27,31,35-nonamethyl-hexatriaconta-2,6,10,14,18,22,26,30,34-nonaen-1-yl) ester
Conditions | Yield |
---|---|
With pyridine; dmap at 20℃; for 6h; | 80% |
With dmap; triethylamine In dichloromethane at 20℃; for 48h; | 70% |
With pyridine; dmap at 20℃; for 6h; | |
With dmap; triethylamine In dichloromethane; N,N-dimethyl-formamide at 20℃; for 48h; Inert atmosphere; |
solanesol
3-methoxycinnamic acid
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 6h; | 80% |
solanesol
phenylpropyolic acid
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 25℃; for 6h; | 69% |
solanesol
3-Methylbutenoic acid
3-methyl-but-2-enoic acid 3,7,11,15,19,23,27,31,35-nonamethyl-hexatriaconta-2,6,10,14,18,22,26,30,34-nonaen-1-yl ester
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 6h; | 66.3% |
solanesol
3-(4'-methoxyphenyl)propenoic acid
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 6h; | 64% |
Conditions | Yield |
---|---|
Stage #1: solanesol; 2,3-dimethoxy-5-methylbenzene-1,4-diol With phosphotungstic acid In nitromethane; n-heptane; water at 40℃; for 3h; Stage #2: With acetic acid; silver(l) oxide In n-heptane at 20℃; for 1h; Product distribution / selectivity; | 63% |
With acetic acid; zinc(II) chloride Behandeln des Reaktionsprodukts mit Ag2O in Aether; |
solanesol
2,3,4,5-tetramethoxytoluene
Conditions | Yield |
---|---|
With bismuth(lll) trifluoromethanesulfonate In nitromethane; hexane at 50℃; for 12h; Product distribution / selectivity; | 62.9% |
With scandium tris(trifluoromethanesulfonate) In nitromethane; hexane at 50℃; for 16h; Product distribution / selectivity; | 32% |
With bismuth(lll) trifluoromethanesulfonate In nitromethane; n-heptane at 50℃; for 12h; Product distribution / selectivity; |
solanesol
3-(2'-methoxyphenyl)propenoic acid
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 6h; | 61% |
solanesol
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 6h; | 60% |
3,4,5-trimethoxycinnamic acid
solanesol
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 6h; | 60% |
solanesol
2,3,4-trimethoxy-6-methylphenol
2,3,4-trimethoxy-6-methyl-5-solanesylphenol
Conditions | Yield |
---|---|
With scandium tris(trifluoromethanesulfonate) In nitromethane; hexane at 50℃; for 16h; Product distribution / selectivity; | 51% |
With bismuth(lll) trifluoromethanesulfonate In nitromethane; n-heptane at 50℃; for 12h; Product distribution / selectivity; |
solanesol
3-(2-furyl)acrylic acid
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 6h; | 50% |
Conditions | Yield |
---|---|
Stage #1: solanesol With pyridine; dmap In dichloromethane at 5℃; for 0.166667h; Sealed tube; Inert atmosphere; Stage #2: methyl chloroformate In dichloromethane at 5 - 20℃; for 1.16667h; Sealed tube; Inert atmosphere; | 46% |
solanesol
2,3-dimethoxy-5-methylbenzene-1,4-diol
A
ubiquinone-45
B
ubiquinone-9
Conditions | Yield |
---|---|
With scandium tris(trifluoromethanesulfonate) In nitromethane; hexane at 50℃; for 16h; | A 11.6% B 40.4% |
Conditions | Yield |
---|---|
Stage #1: solanesol; tetrabutylammonium dihydrogen phosphate With trichloroacetonitrile In dichloromethane at 20℃; for 1h; Inert atmosphere; Darkness; Stage #2: With ammonium hydroxide In tetrahydrofuran; water at 20℃; for 14h; Inert atmosphere; | 33% |
Conditions | Yield |
---|---|
Stage #1: solanesol With tetrabutylammonium dihydrogen phosphate; trichloroacetonitrile In dichloromethane at 20℃; for 14h; Darkness; Stage #2: ammonium hydroxide In tetrahydrofuran; dichloromethane at 20℃; for 0.5h; | 32% |
Conditions | Yield |
---|---|
Stage #1: solanesol; tetrabutylammonium dihydrogen phosphate With trichloroacetonitrile In dichloromethane at 20℃; for 14h; Inert atmosphere; Darkness; Stage #2: With ammonium hydroxide In tetrahydrofuran; methanol; water; toluene at 20℃; for 1h; Inert atmosphere; | 27% |
solanesol
3,4,5-triiodobenzoyl chloride
3,4,5-triiodo-benzoic acid-(3,7,11,15,19,23,27,31,35-nonamethyl-hexatriaconta-2t,6t,10t,14t,18t,22t,26t,30t,34-nonaenyl ester)
solanesol
solanesylaldehyd
Conditions | Yield |
---|---|
With manganese(IV) oxide |
solanesol
decaprenol
Conditions | Yield |
---|---|
ueber mehrere Zwischenstufen; | |
Multi-step reaction with 5 steps 1: PBr3 / pyridine / diethyl ether; petroleum ether / 2 h / 0 °C 2: Na / ethanol / 1,) 0 deg C, 3 h, 2.) 60 deg C, 4 h, 3.) r.t., overnight 3: 10percent aq. NaOH / ethanol / 1.) r.t., 2 h, 2.) 60 deg C, 3 h 4: 89 percent / NaH / tetrahydrofuran / 5 h / Heating 5: i-Bu2AlH / petroleum ether; cyclopentane / 3 h / Heating View Scheme | |
Multi-step reaction with 3 steps 1: 1.1 g / PBr3 / tetrahydrofuran / 0.42 h / -20 °C 2: 70 percent / 1.) n-BuLi / tetrahydrofuran; hexane / 1.) -70 deg C, 40 min, 2.) 40 min 3: Na / ethanol; tetrahydrofuran / 0.25 h / -40 °C View Scheme |
solanesol
2,6,10,14,18,22,26,30,34-nonamethyl-hexatriacontane
Conditions | Yield |
---|---|
With palladium on activated charcoal; ethanol Hydrogenation; |
solanesol
3,7,11,15,19,23,27,31,35-nonamethyl-hexatriacontan-1-ol
Conditions | Yield |
---|---|
With palladium on activated charcoal Hydrogenation; |
solanesol
3,5-dinitro-benzoic acid-(3,7,11,15,19,23,27,31,35-nonamethyl-hexatriaconta-2t,6t,10t,14t,18t,22t,26t,30t,34-nonaenyl ester)
solanesol
3-nitrophthalic acid anhydride
Molecular Formula: C45H74O
Molecular Weight: 631.07 g/mol
Index of Refraction: 1.506
Density: 0.889 g/cm3
Flash Point: 130.2 °C
Enthalpy of Vaporization: 114.99 kJ/mol
Boiling Point: 685.6 °C at 760 mmHg
Vapour Pressure: 9.21E-22 mmHg at 25 °C
Melting point: 33 °C
Storage tempreture: -20 °C
Appearance: Brown waxy solid
Structure of Solanesol (CAS NO.13190-97-1):
Product Category of Solanesol (CAS NO.13190-97-1): Miscellaneous Natural Products;Nicotine Derivatives;Biochemistry;Terpenes;Natural Plant Extract
Solanesol (CAS NO.13190-97-1) is ahigh molecular weight isoprenoid alcohol isolated from tobacco leaf.
RTECS : MP5366666
Solanesol , its cas register number is 13190-97-1. It also can be called 3,7,11,15,19,23,27,31,35-Nonamethylhexatriaconta-2,6,10,14,18,22,26,30,34-nonaen-1-ol .
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