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CAS No.: | 97134-11-7 |
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Name: | Pinellic acid |
Article Data: | 11 |
Molecular Structure: | |
Formula: | C18H34O5 |
Molecular Weight: | 330.465 |
PSA: | 97.99000 |
LogP: | 3.02090 |
methyl (9S,10E,12S,13S)-9,12,13-trihydroxy-10-octadecenoate
(9S,10E,12S,13S)-(-)-9,12,13-trihydroxy-10-octadecenoic acid
Conditions | Yield |
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Stage #1: methyl (9S,10E,12S,13S)-9,12,13-trihydroxy-10-octadecenoate With sodium hydroxide; water In methanol at 40℃; for 5h; Stage #2: With hydrogenchloride; water In methanol at 0℃; | 85% |
(9S,12S,13S)-(E)-9,12,13-trihydroxy-10-octadecenoic acid tert-butyl ester
(9S,10E,12S,13S)-(-)-9,12,13-trihydroxy-10-octadecenoic acid
Conditions | Yield |
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With potassium hydroxide In ethanol at 20℃; for 46h; | 82% |
With potassium hydroxide In ethanol; water at 20℃; for 46h; | 82% |
9(S)-hydroperoxyoctadeca-10Z,12E-dienoic acid
(9S,10E,12S,13S)-(-)-9,12,13-trihydroxy-10-octadecenoic acid
Conditions | Yield |
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With enzyme preparation from beetroot (Beta vulgaris spp. vulgaris var. vulgaris) at 23℃; for 1h; pH=6.7; aq. phosphate buffer; Enzymatic reaction; stereospecific reaction; | 80% |
(S,E)-9-(tert-butyldiphenylsilyloxy)-11-((4S,5S)-2,2-dimethyl-5-pentyl-1,3-dioxolan-4-yl)undec-10-enoic acid
(9S,10E,12S,13S)-(-)-9,12,13-trihydroxy-10-octadecenoic acid
Conditions | Yield |
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With hydrogenchloride In methanol at 20℃; | 78% |
hydrogenchloride In methanol at 20℃; |
(9S,10E)-11-[(4S,5S)-2,2-dimethyl-5-pentyl-1,3-dioxolan-4-yl]-9-(methoxymethoxy)undec-10-enoic acid
(9S,10E,12S,13S)-(-)-9,12,13-trihydroxy-10-octadecenoic acid
Conditions | Yield |
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With hydrogenchloride In methanol at 20℃; for 10h; | 66% |
(S)-11-(4-methoxybenzyloxy)undec-1-yn-3-ol
(9S,10E,12S,13S)-(-)-9,12,13-trihydroxy-10-octadecenoic acid
Conditions | Yield |
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Multi-step reaction with 8 steps 1: 98 percent / imidazole / CH2Cl2 / 0 °C 2: 86 percent / CuI; Et3N / Pd(PPh3)2Cl2 / 6 h 3: 91 percent / K3Fe(CN)6; aq. K2CO3; MeSO2NH2 / OsO4; (DHQ)2PHAL / 2-methyl-propan-2-ol; toluene / 24 h / 0 °C 4: 90 percent / Li; liq. NH3 / tetrahydrofuran / 1 h / -78 °C 5: 92 percent / TsOH / CH2Cl2 / 20 °C 6: IBX / ethyl acetate / 5 h / Heating 7: 174 mg / aq. NaClO2; NaH2PO4 / dimethylsulfoxide / 20 °C 8: 78 percent / aq. HCl / methanol / 20 °C View Scheme | |
Multi-step reaction with 7 steps 1.1: 98 percent / imidazole / CH2Cl2 / 0 - 20 °C 2.1: 86 percent / triethylamine / Pd(PPh3)2Cl2; CuI / 6 h 3.1: 96 percent / (DHQ)2PHAL; K2CO3; MeSO2NH2 / K3Fe(CN)6; OsO4 / 2-methyl-propan-2-ol; toluene; H2O / 24 h / 0 °C 4.1: 89 percent / Na; NH3 / tetrahydrofuran / -40 °C 5.1: 92 percent / p-TSA / CH2Cl2 6.1: (COCl)2; DMSO; triethylamine / CH2Cl2 / -78 - -60 °C 6.2: NaClO2; NaH2PO4 / dimethylsulfoxide / 20 °C 7.1: HCl / methanol / 20 °C View Scheme |
(E)-ethyl 11-(4-methoxybenzyloxy)undec-2-enoate
(9S,10E,12S,13S)-(-)-9,12,13-trihydroxy-10-octadecenoic acid
Conditions | Yield |
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Multi-step reaction with 13 steps 1: 96 percent / K3Fe(CN)6; aq. K2CO3; MeSO2NH2 / OsO4; (DHQ)2PHAL / 2-methyl-propan-2-ol; toluene / 24 h / 0 °C 2: 94 percent / TsOH / CH2Cl2 / 20 °C 3: 95 percent / DIBAL-H / CH2Cl2; toluene / 2 h / 0 - 20 °C 4: 89 percent / N-chlorosuccinimide; PPh3 / CH2Cl2 / 3 h / 0 - 20 °C 5: 82 percent / n-BuLi; HMPA / tetrahydrofuran; hexane / -42 - 20 °C 6: 98 percent / imidazole / CH2Cl2 / 0 °C 7: 86 percent / CuI; Et3N / Pd(PPh3)2Cl2 / 6 h 8: 91 percent / K3Fe(CN)6; aq. K2CO3; MeSO2NH2 / OsO4; (DHQ)2PHAL / 2-methyl-propan-2-ol; toluene / 24 h / 0 °C 9: 90 percent / Li; liq. NH3 / tetrahydrofuran / 1 h / -78 °C 10: 92 percent / TsOH / CH2Cl2 / 20 °C 11: IBX / ethyl acetate / 5 h / Heating 12: 174 mg / aq. NaClO2; NaH2PO4 / dimethylsulfoxide / 20 °C 13: 78 percent / aq. HCl / methanol / 20 °C View Scheme | |
Multi-step reaction with 12 steps 1.1: 96 percent / (DHQ)2PHAL; K2CO3; MeSO2NH2 / K3Fe(CN)6; OsO4 / 2-methyl-propan-2-ol; toluene; H2O / 24 h / 0 °C 2.1: 96 percent / p-TSA / CH2Cl2 3.1: 96 percent / DIBAL-H / CH2Cl2 / 2 h / 0 - 20 °C 4.1: 89 percent / N-chlorosuccinimide; PPh3 / CH2Cl2 / 3 h / 0 - 20 °C 5.1: 82 percent / nBuLi; HMPA / tetrahydrofuran / 0.5 h / -42 - 20 °C 6.1: 98 percent / imidazole / CH2Cl2 / 0 - 20 °C 7.1: 86 percent / triethylamine / Pd(PPh3)2Cl2; CuI / 6 h 8.1: 96 percent / (DHQ)2PHAL; K2CO3; MeSO2NH2 / K3Fe(CN)6; OsO4 / 2-methyl-propan-2-ol; toluene; H2O / 24 h / 0 °C 9.1: 89 percent / Na; NH3 / tetrahydrofuran / -40 °C 10.1: 92 percent / p-TSA / CH2Cl2 11.1: (COCl)2; DMSO; triethylamine / CH2Cl2 / -78 - -60 °C 11.2: NaClO2; NaH2PO4 / dimethylsulfoxide / 20 °C 12.1: HCl / methanol / 20 °C View Scheme |
((4S,5S)-5-(8-(4-methoxybenzyloxy)octyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methanol
(9S,10E,12S,13S)-(-)-9,12,13-trihydroxy-10-octadecenoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 10 steps 1: 89 percent / N-chlorosuccinimide; PPh3 / CH2Cl2 / 3 h / 0 - 20 °C 2: 82 percent / n-BuLi; HMPA / tetrahydrofuran; hexane / -42 - 20 °C 3: 98 percent / imidazole / CH2Cl2 / 0 °C 4: 86 percent / CuI; Et3N / Pd(PPh3)2Cl2 / 6 h 5: 91 percent / K3Fe(CN)6; aq. K2CO3; MeSO2NH2 / OsO4; (DHQ)2PHAL / 2-methyl-propan-2-ol; toluene / 24 h / 0 °C 6: 90 percent / Li; liq. NH3 / tetrahydrofuran / 1 h / -78 °C 7: 92 percent / TsOH / CH2Cl2 / 20 °C 8: IBX / ethyl acetate / 5 h / Heating 9: 174 mg / aq. NaClO2; NaH2PO4 / dimethylsulfoxide / 20 °C 10: 78 percent / aq. HCl / methanol / 20 °C View Scheme | |
Multi-step reaction with 9 steps 1.1: 89 percent / N-chlorosuccinimide; PPh3 / CH2Cl2 / 3 h / 0 - 20 °C 2.1: 82 percent / nBuLi; HMPA / tetrahydrofuran / 0.5 h / -42 - 20 °C 3.1: 98 percent / imidazole / CH2Cl2 / 0 - 20 °C 4.1: 86 percent / triethylamine / Pd(PPh3)2Cl2; CuI / 6 h 5.1: 96 percent / (DHQ)2PHAL; K2CO3; MeSO2NH2 / K3Fe(CN)6; OsO4 / 2-methyl-propan-2-ol; toluene; H2O / 24 h / 0 °C 6.1: 89 percent / Na; NH3 / tetrahydrofuran / -40 °C 7.1: 92 percent / p-TSA / CH2Cl2 8.1: (COCl)2; DMSO; triethylamine / CH2Cl2 / -78 - -60 °C 8.2: NaClO2; NaH2PO4 / dimethylsulfoxide / 20 °C 9.1: HCl / methanol / 20 °C View Scheme |
(4S,5R)-4-(8-(4-methoxybenzyloxy)octyl)-5-(chloromethyl)-2,2-dimethyl-1,3-dioxolane
(9S,10E,12S,13S)-(-)-9,12,13-trihydroxy-10-octadecenoic acid
Conditions | Yield |
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Multi-step reaction with 9 steps 1: 82 percent / n-BuLi; HMPA / tetrahydrofuran; hexane / -42 - 20 °C 2: 98 percent / imidazole / CH2Cl2 / 0 °C 3: 86 percent / CuI; Et3N / Pd(PPh3)2Cl2 / 6 h 4: 91 percent / K3Fe(CN)6; aq. K2CO3; MeSO2NH2 / OsO4; (DHQ)2PHAL / 2-methyl-propan-2-ol; toluene / 24 h / 0 °C 5: 90 percent / Li; liq. NH3 / tetrahydrofuran / 1 h / -78 °C 6: 92 percent / TsOH / CH2Cl2 / 20 °C 7: IBX / ethyl acetate / 5 h / Heating 8: 174 mg / aq. NaClO2; NaH2PO4 / dimethylsulfoxide / 20 °C 9: 78 percent / aq. HCl / methanol / 20 °C View Scheme | |
Multi-step reaction with 8 steps 1.1: 82 percent / nBuLi; HMPA / tetrahydrofuran / 0.5 h / -42 - 20 °C 2.1: 98 percent / imidazole / CH2Cl2 / 0 - 20 °C 3.1: 86 percent / triethylamine / Pd(PPh3)2Cl2; CuI / 6 h 4.1: 96 percent / (DHQ)2PHAL; K2CO3; MeSO2NH2 / K3Fe(CN)6; OsO4 / 2-methyl-propan-2-ol; toluene; H2O / 24 h / 0 °C 5.1: 89 percent / Na; NH3 / tetrahydrofuran / -40 °C 6.1: 92 percent / p-TSA / CH2Cl2 7.1: (COCl)2; DMSO; triethylamine / CH2Cl2 / -78 - -60 °C 7.2: NaClO2; NaH2PO4 / dimethylsulfoxide / 20 °C 8.1: HCl / methanol / 20 °C View Scheme |
(4R,5S)-ethyl 5-(8-(4-methoxybenzyloxy)octyl)-2,2-dimethyl-1,3-dioxolane-4-carboxylate
(9S,10E,12S,13S)-(-)-9,12,13-trihydroxy-10-octadecenoic acid
Conditions | Yield |
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Multi-step reaction with 11 steps 1: 95 percent / DIBAL-H / CH2Cl2; toluene / 2 h / 0 - 20 °C 2: 89 percent / N-chlorosuccinimide; PPh3 / CH2Cl2 / 3 h / 0 - 20 °C 3: 82 percent / n-BuLi; HMPA / tetrahydrofuran; hexane / -42 - 20 °C 4: 98 percent / imidazole / CH2Cl2 / 0 °C 5: 86 percent / CuI; Et3N / Pd(PPh3)2Cl2 / 6 h 6: 91 percent / K3Fe(CN)6; aq. K2CO3; MeSO2NH2 / OsO4; (DHQ)2PHAL / 2-methyl-propan-2-ol; toluene / 24 h / 0 °C 7: 90 percent / Li; liq. NH3 / tetrahydrofuran / 1 h / -78 °C 8: 92 percent / TsOH / CH2Cl2 / 20 °C 9: IBX / ethyl acetate / 5 h / Heating 10: 174 mg / aq. NaClO2; NaH2PO4 / dimethylsulfoxide / 20 °C 11: 78 percent / aq. HCl / methanol / 20 °C View Scheme | |
Multi-step reaction with 10 steps 1.1: 96 percent / DIBAL-H / CH2Cl2 / 2 h / 0 - 20 °C 2.1: 89 percent / N-chlorosuccinimide; PPh3 / CH2Cl2 / 3 h / 0 - 20 °C 3.1: 82 percent / nBuLi; HMPA / tetrahydrofuran / 0.5 h / -42 - 20 °C 4.1: 98 percent / imidazole / CH2Cl2 / 0 - 20 °C 5.1: 86 percent / triethylamine / Pd(PPh3)2Cl2; CuI / 6 h 6.1: 96 percent / (DHQ)2PHAL; K2CO3; MeSO2NH2 / K3Fe(CN)6; OsO4 / 2-methyl-propan-2-ol; toluene; H2O / 24 h / 0 °C 7.1: 89 percent / Na; NH3 / tetrahydrofuran / -40 °C 8.1: 92 percent / p-TSA / CH2Cl2 9.1: (COCl)2; DMSO; triethylamine / CH2Cl2 / -78 - -60 °C 9.2: NaClO2; NaH2PO4 / dimethylsulfoxide / 20 °C 10.1: HCl / methanol / 20 °C View Scheme |