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CAS No.: | 11076-19-0 | ||
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Name: | BONGKREKIC ACID | ||
Article Data: | 8 | ||
Molecular Structure: | |||
Formula: | C28H38 O7 | ||
Molecular Weight: | 486.606 | ||
Synonyms: | 2,4,8,10,14,18,20-Docosaheptaenedioicacid, 20-(carboxymethyl)-6-methoxy-2,5,17-trimethyl-,[R-[R*,S*-(E,Z,Z,E,E,Z,E)]]-; Bongkrekic acid (6CI,8CI) | ||
Density: | 1.114g/cm3 | ||
Melting Point: | 50-60° | ||
Boiling Point: | 715.1°Cat760mmHg | ||
Flash Point: | 231°C | ||
Safety: |
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PSA: | 121.13000 | ||
LogP: | 5.88560 |
bongkrekic acid
Conditions | Yield |
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With hydrogenchloride; water In tetrahydrofuran at 0 - 20℃; for 1h; | 92% |
(Z)-3-[(1E,3S,5E,9E,11Z,14R,15Z,17E)-19-tert-butoxy-14-methoxy-3,15,18-trimethyl-19-oxononadeca-1,5,9,11,15,17-hexaenyl]pent-2-enedioic acid
bongkrekic acid
Conditions | Yield |
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With hydrogenchloride; water In tetrahydrofuran at 20℃; for 3h; | 83% |
(2E,4Z,8Z,10E,14E)-(6R,17S)-17-(4-Carboxymethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-6-methoxy-2,5-dimethyl-octadeca-2,4,8,10,14-pentaenoic acid
bongkrekic acid
Conditions | Yield |
---|---|
With potassium methanolate In tetrahydrofuran; methanol at 0℃; for 0.0833333h; | 65% |
Conditions | Yield |
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Stage #1: C31H44O7 With water; potassium hydroxide In 1,2-dimethoxyethane at 20℃; for 8h; Stage #2: With hydrogenchloride In 1,2-dimethoxyethane; water optical yield given as %de; Further stages; | A 17% B 35% |
Conditions | Yield |
---|---|
With potassium hydroxide In 1,2-dimethoxyethane; water at 20℃; for 8h; | A 35% B 17% |
(2E,4Z,8Z,10E,14E,18E,20Z)-(6R,17S)-20-Carboxymethyl-6-methoxy-2,5,17-trimethyl-docosa-2,4,8,10,14,18,20-heptaenedioic acid 1-tert-butyl ester 22-(tert-butyl-diphenyl-silanyloxymethyl) ester
bongkrekic acid
Conditions | Yield |
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With hydrogenchloride In methanol; water at 20℃; |
bongkrekic acid
Conditions | Yield |
---|---|
Multi-step reaction with 11 steps 1.1: 86 percent / BuLi; HMPA / tetrahydrofuran 2.1: DIBAH / tetrahydrofuran 2.2: 70 percent / NaBH4 / tetrahydrofuran; H2O 3.1: Dess-Martin reagent / benzene; CH2Cl2 4.1: 80 percent / benzene 5.1: 82 percent / HCl / H2O; tetrahydrofuran 6.1: MnO2 / benzene; CH2Cl2 6.2: NaClO2; NaH2PO4; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol; H2O 6.3: 40 percent / Et3N / tetrahydrofuran 7.1: Dess-Martin reagent / benzene; CH2Cl2 7.2: NaClO2; NaH2PO4; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol; H2O 8.1: HCl / H2O; methanol / 20 °C View Scheme | |
Multi-step reaction with 14 steps 1.1: 86 percent / BuLi; HMPA / tetrahydrofuran 2.1: DIBAH / tetrahydrofuran 2.2: 70 percent / NaBH4 / tetrahydrofuran; H2O 3.1: 93 percent / Na-Hg; Na2HPO4 / methanol 4.1: 96 percent / Et3N / CH2Cl2 5.1: 83 percent / 2,6-di-tert-butylpyridine / benzene 6.1: 81 percent / DIBAH / tetrahydrofuran 7.1: Dess-Martin reagent / benzene; CH2Cl2 8.1: 80 percent / benzene 9.1: 82 percent / HCl / H2O; tetrahydrofuran 10.1: MnO2 / benzene; CH2Cl2 10.2: NaClO2; NaH2PO4; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol; H2O 10.3: 40 percent / Et3N / tetrahydrofuran 11.1: Dess-Martin reagent / benzene; CH2Cl2 11.2: NaClO2; NaH2PO4; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol; H2O 12.1: HCl / H2O; methanol / 20 °C View Scheme |
(R)-5-((Z)-4-Hydroxy-but-2-enyl)-4-methyl-5H-furan-2-one
bongkrekic acid
Conditions | Yield |
---|---|
Multi-step reaction with 12 steps 1.1: MnO2 / CH2Cl2 2.1: 86 percent / BuLi; HMPA / tetrahydrofuran 3.1: DIBAH / tetrahydrofuran 3.2: 70 percent / NaBH4 / tetrahydrofuran; H2O 4.1: Dess-Martin reagent / benzene; CH2Cl2 5.1: 80 percent / benzene 6.1: 82 percent / HCl / H2O; tetrahydrofuran 7.1: MnO2 / benzene; CH2Cl2 7.2: NaClO2; NaH2PO4; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol; H2O 7.3: 40 percent / Et3N / tetrahydrofuran 8.1: Dess-Martin reagent / benzene; CH2Cl2 8.2: NaClO2; NaH2PO4; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol; H2O 9.1: HCl / H2O; methanol / 20 °C View Scheme | |
Multi-step reaction with 15 steps 1.1: MnO2 / CH2Cl2 2.1: 86 percent / BuLi; HMPA / tetrahydrofuran 3.1: DIBAH / tetrahydrofuran 3.2: 70 percent / NaBH4 / tetrahydrofuran; H2O 4.1: 93 percent / Na-Hg; Na2HPO4 / methanol 5.1: 96 percent / Et3N / CH2Cl2 6.1: 83 percent / 2,6-di-tert-butylpyridine / benzene 7.1: 81 percent / DIBAH / tetrahydrofuran 8.1: Dess-Martin reagent / benzene; CH2Cl2 9.1: 80 percent / benzene 10.1: 82 percent / HCl / H2O; tetrahydrofuran 11.1: MnO2 / benzene; CH2Cl2 11.2: NaClO2; NaH2PO4; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol; H2O 11.3: 40 percent / Et3N / tetrahydrofuran 12.1: Dess-Martin reagent / benzene; CH2Cl2 12.2: NaClO2; NaH2PO4; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol; H2O 13.1: HCl / H2O; methanol / 20 °C View Scheme |
(R)-5-((2Z,4E)-6-Bromo-hexa-2,4-dienyl)-4-methyl-5H-furan-2-one
bongkrekic acid
Conditions | Yield |
---|---|
Multi-step reaction with 9 steps 1.1: 86 percent / BuLi; HMPA / tetrahydrofuran 2.1: DIBAH / tetrahydrofuran 2.2: 70 percent / NaBH4 / tetrahydrofuran; H2O 3.1: Dess-Martin reagent / benzene; CH2Cl2 4.1: 80 percent / benzene 5.1: 82 percent / HCl / H2O; tetrahydrofuran 6.1: MnO2 / benzene; CH2Cl2 6.2: NaClO2; NaH2PO4; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol; H2O 6.3: 40 percent / Et3N / tetrahydrofuran 7.1: Dess-Martin reagent / benzene; CH2Cl2 7.2: NaClO2; NaH2PO4; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol; H2O 8.1: HCl / H2O; methanol / 20 °C View Scheme | |
Multi-step reaction with 12 steps 1.1: 86 percent / BuLi; HMPA / tetrahydrofuran 2.1: DIBAH / tetrahydrofuran 2.2: 70 percent / NaBH4 / tetrahydrofuran; H2O 3.1: 93 percent / Na-Hg; Na2HPO4 / methanol 4.1: 96 percent / Et3N / CH2Cl2 5.1: 83 percent / 2,6-di-tert-butylpyridine / benzene 6.1: 81 percent / DIBAH / tetrahydrofuran 7.1: Dess-Martin reagent / benzene; CH2Cl2 8.1: 80 percent / benzene 9.1: 82 percent / HCl / H2O; tetrahydrofuran 10.1: MnO2 / benzene; CH2Cl2 10.2: NaClO2; NaH2PO4; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol; H2O 10.3: 40 percent / Et3N / tetrahydrofuran 11.1: Dess-Martin reagent / benzene; CH2Cl2 11.2: NaClO2; NaH2PO4; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol; H2O 12.1: HCl / H2O; methanol / 20 °C View Scheme |
(2E,6E)-(S)-5-Methyl-7-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-hepta-2,6-dien-1-ol
bongkrekic acid
Conditions | Yield |
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Multi-step reaction with 11 steps 1.1: 92 percent / Et3N / PdCl2(PPh3)2 / methanol 2.1: MsCl; iPr2EtN; 4-DMAP / CH2Cl2 2.2: 81 percent / dimethylformamide 3.1: 86 percent / BuLi; HMPA / tetrahydrofuran 4.1: DIBAH / tetrahydrofuran 4.2: 70 percent / NaBH4 / tetrahydrofuran; H2O 5.1: Dess-Martin reagent / benzene; CH2Cl2 6.1: 80 percent / benzene 7.1: 82 percent / HCl / H2O; tetrahydrofuran 8.1: MnO2 / benzene; CH2Cl2 8.2: NaClO2; NaH2PO4; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol; H2O 8.3: 40 percent / Et3N / tetrahydrofuran 9.1: Dess-Martin reagent / benzene; CH2Cl2 9.2: NaClO2; NaH2PO4; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol; H2O 10.1: HCl / H2O; methanol / 20 °C View Scheme | |
Multi-step reaction with 14 steps 1.1: 92 percent / Et3N / PdCl2(PPh3)2 / methanol 2.1: MsCl; iPr2EtN; 4-DMAP / CH2Cl2 2.2: 81 percent / dimethylformamide 3.1: 86 percent / BuLi; HMPA / tetrahydrofuran 4.1: DIBAH / tetrahydrofuran 4.2: 70 percent / NaBH4 / tetrahydrofuran; H2O 5.1: 93 percent / Na-Hg; Na2HPO4 / methanol 6.1: 96 percent / Et3N / CH2Cl2 7.1: 83 percent / 2,6-di-tert-butylpyridine / benzene 8.1: 81 percent / DIBAH / tetrahydrofuran 9.1: Dess-Martin reagent / benzene; CH2Cl2 10.1: 80 percent / benzene 11.1: 82 percent / HCl / H2O; tetrahydrofuran 12.1: MnO2 / benzene; CH2Cl2 12.2: NaClO2; NaH2PO4; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol; H2O 12.3: 40 percent / Et3N / tetrahydrofuran 13.1: Dess-Martin reagent / benzene; CH2Cl2 13.2: NaClO2; NaH2PO4; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol; H2O 14.1: HCl / H2O; methanol / 20 °C View Scheme |