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CAS No.: | 743-51-1 |
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Name: | BYSSOCHLAMICACID |
Article Data: | 4 |
Molecular Structure: | |
Formula: | C18H20 O6 |
Molecular Weight: | 332.353 |
Synonyms: | 1,5-Cyclononadiene-1,2,5,6-tetracarboxylic1,2:5,6-dianhydride, 8-ethyl-3-propyl- (7CI,8CI);1H-Cyclonona[1,2-c:5,6-c']difuran-1,3,6,8(4H)-tetrone,10-ethyl-5,9,10,11-tetrahydro-4-propyl-, [4S-(4R*,10S*)]-; (+)-ByssochlamicAcid; Byssochlamic acid |
PSA: | 86.74000 |
LogP: | 2.37280 |
(+)-byssochlamic acid
Conditions | Yield |
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With hydrogenchloride dehydrative cyclization; |
Conditions | Yield |
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Multi-step reaction with 16 steps 1.1: 93 percent / NaH / benzene / 1.5 h / Heating 2.1: Br2 / diethyl ether / 2.17 h / 0 °C 3.1: 39 percent / methanol / 0 - 20 °C 4.1: 98 percent / porcine liver esterase; aq. Na2HPO4; aq. K2HPO4 / acetone / 3 h / 20 °C / pH 7 5.1: triethylamine / tetrahydrofuran / 0.5 h / 0 °C 5.2: 89 percent / NaBH4 / H2O / 0.5 h / 0 °C 6.1: 93 percent / TsOH monohydrate / CH2Cl2 / 1 h / 20 °C 7.1: DIBAL-H / CH2Cl2; hexane / 1 h / -78 °C 7.2: 91 percent / Rochelle's salt / CH2Cl2 / 0.33 h 8.1: 95 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 9.1: 71 percent / MgBr2 / diethyl ether / 5 h / 20 °C 10.1: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C 11.1: aq. HF / acetonitrile / 1.5 h / 20 °C 12.1: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating 13.1: CH2Cl2 / Photolysis 14.1: aq. LiOH / dioxane / 1.5 h / 50 °C 15.1: KMnO4 / H2O; dioxane / 1 h / 40 °C 16.1: aq. HCl View Scheme | |
Multi-step reaction with 16 steps 1.1: 93 percent / NaH / benzene / 1.5 h / Heating 2.1: Br2 / diethyl ether / 2.17 h / 0 °C 3.1: 39 percent / methanol / 0 - 20 °C 4.1: 98 percent / porcine liver esterase; aq. Na2HPO4; aq. K2HPO4 / acetone / 3 h / 20 °C / pH 7 5.1: triethylamine / tetrahydrofuran / 0.5 h / 0 °C 5.2: 89 percent / NaBH4 / H2O / 0.5 h / 0 °C 6.1: 93 percent / TsOH monohydrate / CH2Cl2 / 1 h / 20 °C 7.1: DIBAL-H / CH2Cl2; hexane / 1 h / -78 °C 7.2: 91 percent / Rochelle's salt / CH2Cl2 / 0.33 h 8.1: 95 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 9.1: 71 percent / MgBr2 / diethyl ether / 5 h / 20 °C 10.1: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C 11.1: aq. HF / acetonitrile / 1.5 h / 20 °C 12.1: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating 13.1: CH2Cl2 / Photolysis 13.2: toluene / Heating 14.1: aq. LiOH / dioxane / 1.5 h / 50 °C 15.1: KMnO4 / H2O; dioxane / 1 h / 40 °C 16.1: aq. HCl View Scheme |
methyl 5-ethyl-2-oxo-cyclohexancarboxylate
(+)-byssochlamic acid
Conditions | Yield |
---|---|
Multi-step reaction with 15 steps 1.1: Br2 / diethyl ether / 2.17 h / 0 °C 2.1: 39 percent / methanol / 0 - 20 °C 3.1: 98 percent / porcine liver esterase; aq. Na2HPO4; aq. K2HPO4 / acetone / 3 h / 20 °C / pH 7 4.1: triethylamine / tetrahydrofuran / 0.5 h / 0 °C 4.2: 89 percent / NaBH4 / H2O / 0.5 h / 0 °C 5.1: 93 percent / TsOH monohydrate / CH2Cl2 / 1 h / 20 °C 6.1: DIBAL-H / CH2Cl2; hexane / 1 h / -78 °C 6.2: 91 percent / Rochelle's salt / CH2Cl2 / 0.33 h 7.1: 95 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 8.1: 71 percent / MgBr2 / diethyl ether / 5 h / 20 °C 9.1: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C 10.1: aq. HF / acetonitrile / 1.5 h / 20 °C 11.1: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating 12.1: CH2Cl2 / Photolysis 13.1: aq. LiOH / dioxane / 1.5 h / 50 °C 14.1: KMnO4 / H2O; dioxane / 1 h / 40 °C 15.1: aq. HCl View Scheme | |
Multi-step reaction with 15 steps 1.1: Br2 / diethyl ether / 2.17 h / 0 °C 2.1: 39 percent / methanol / 0 - 20 °C 3.1: 98 percent / porcine liver esterase; aq. Na2HPO4; aq. K2HPO4 / acetone / 3 h / 20 °C / pH 7 4.1: triethylamine / tetrahydrofuran / 0.5 h / 0 °C 4.2: 89 percent / NaBH4 / H2O / 0.5 h / 0 °C 5.1: 93 percent / TsOH monohydrate / CH2Cl2 / 1 h / 20 °C 6.1: DIBAL-H / CH2Cl2; hexane / 1 h / -78 °C 6.2: 91 percent / Rochelle's salt / CH2Cl2 / 0.33 h 7.1: 95 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 8.1: 71 percent / MgBr2 / diethyl ether / 5 h / 20 °C 9.1: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C 10.1: aq. HF / acetonitrile / 1.5 h / 20 °C 11.1: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating 12.1: CH2Cl2 / Photolysis 12.2: toluene / Heating 13.1: aq. LiOH / dioxane / 1.5 h / 50 °C 14.1: KMnO4 / H2O; dioxane / 1 h / 40 °C 15.1: aq. HCl View Scheme |
3-n-propylcyclobut-1-en-1,2-dicarboxylic acid
(+)-byssochlamic acid
Conditions | Yield |
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Multi-step reaction with 9 steps 1: 59 percent / NaI; DIPEA / 1,2-dimethoxy-ethane / 4 h / 20 - 70 °C 2: pig liver esteraze; Na2HPO4; K2HPO4 / acetone / 3 h / 20 °C / pH 7 3: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C 4: aq. HF / acetonitrile / 1.5 h / 20 °C 5: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating 6: CH2Cl2 / Photolysis 7: aq. LiOH / dioxane / 1.5 h / 50 °C 8: KMnO4 / H2O; dioxane / 1 h / 40 °C 9: aq. HCl View Scheme | |
Multi-step reaction with 9 steps 1.1: 59 percent / NaI; DIPEA / 1,2-dimethoxy-ethane / 4 h / 20 - 70 °C 2.1: pig liver esteraze; Na2HPO4; K2HPO4 / acetone / 3 h / 20 °C / pH 7 3.1: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C 4.1: aq. HF / acetonitrile / 1.5 h / 20 °C 5.1: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating 6.1: CH2Cl2 / Photolysis 6.2: toluene / Heating 7.1: aq. LiOH / dioxane / 1.5 h / 50 °C 8.1: KMnO4 / H2O; dioxane / 1 h / 40 °C 9.1: aq. HCl View Scheme |
dimethyl 4-ethylcyclopenten-1,2-dicarboxylate
(+)-byssochlamic acid
Conditions | Yield |
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Multi-step reaction with 13 steps 1.1: 98 percent / porcine liver esterase; aq. Na2HPO4; aq. K2HPO4 / acetone / 3 h / 20 °C / pH 7 2.1: triethylamine / tetrahydrofuran / 0.5 h / 0 °C 2.2: 89 percent / NaBH4 / H2O / 0.5 h / 0 °C 3.1: 93 percent / TsOH monohydrate / CH2Cl2 / 1 h / 20 °C 4.1: DIBAL-H / CH2Cl2; hexane / 1 h / -78 °C 4.2: 91 percent / Rochelle's salt / CH2Cl2 / 0.33 h 5.1: 95 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 6.1: 71 percent / MgBr2 / diethyl ether / 5 h / 20 °C 7.1: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C 8.1: aq. HF / acetonitrile / 1.5 h / 20 °C 9.1: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating 10.1: CH2Cl2 / Photolysis 11.1: aq. LiOH / dioxane / 1.5 h / 50 °C 12.1: KMnO4 / H2O; dioxane / 1 h / 40 °C 13.1: aq. HCl View Scheme | |
Multi-step reaction with 13 steps 1.1: 98 percent / porcine liver esterase; aq. Na2HPO4; aq. K2HPO4 / acetone / 3 h / 20 °C / pH 7 2.1: triethylamine / tetrahydrofuran / 0.5 h / 0 °C 2.2: 89 percent / NaBH4 / H2O / 0.5 h / 0 °C 3.1: 93 percent / TsOH monohydrate / CH2Cl2 / 1 h / 20 °C 4.1: DIBAL-H / CH2Cl2; hexane / 1 h / -78 °C 4.2: 91 percent / Rochelle's salt / CH2Cl2 / 0.33 h 5.1: 95 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 6.1: 71 percent / MgBr2 / diethyl ether / 5 h / 20 °C 7.1: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C 8.1: aq. HF / acetonitrile / 1.5 h / 20 °C 9.1: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating 10.1: CH2Cl2 / Photolysis 10.2: toluene / Heating 11.1: aq. LiOH / dioxane / 1.5 h / 50 °C 12.1: KMnO4 / H2O; dioxane / 1 h / 40 °C 13.1: aq. HCl View Scheme |
dimethyl 3-n-propylcyclobut-1-en-1,2-dicarboxylate
(+)-byssochlamic acid
Conditions | Yield |
---|---|
Multi-step reaction with 10 steps 1: 72 percent / aq. LiOH / tetrahydrofuran / 1 h / 0 °C 2: 59 percent / NaI; DIPEA / 1,2-dimethoxy-ethane / 4 h / 20 - 70 °C 3: pig liver esteraze; Na2HPO4; K2HPO4 / acetone / 3 h / 20 °C / pH 7 4: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C 5: aq. HF / acetonitrile / 1.5 h / 20 °C 6: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating 7: CH2Cl2 / Photolysis 8: aq. LiOH / dioxane / 1.5 h / 50 °C 9: KMnO4 / H2O; dioxane / 1 h / 40 °C 10: aq. HCl View Scheme | |
Multi-step reaction with 10 steps 1.1: 72 percent / aq. LiOH / tetrahydrofuran / 1 h / 0 °C 2.1: 59 percent / NaI; DIPEA / 1,2-dimethoxy-ethane / 4 h / 20 - 70 °C 3.1: pig liver esteraze; Na2HPO4; K2HPO4 / acetone / 3 h / 20 °C / pH 7 4.1: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C 5.1: aq. HF / acetonitrile / 1.5 h / 20 °C 6.1: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating 7.1: CH2Cl2 / Photolysis 7.2: toluene / Heating 8.1: aq. LiOH / dioxane / 1.5 h / 50 °C 9.1: KMnO4 / H2O; dioxane / 1 h / 40 °C 10.1: aq. HCl View Scheme |
1,3-Dibromo-5-ethyl-2-oxo-cyclohexanecarboxylic acid methyl ester
(+)-byssochlamic acid
Conditions | Yield |
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Multi-step reaction with 14 steps 1.1: 39 percent / methanol / 0 - 20 °C 2.1: 98 percent / porcine liver esterase; aq. Na2HPO4; aq. K2HPO4 / acetone / 3 h / 20 °C / pH 7 3.1: triethylamine / tetrahydrofuran / 0.5 h / 0 °C 3.2: 89 percent / NaBH4 / H2O / 0.5 h / 0 °C 4.1: 93 percent / TsOH monohydrate / CH2Cl2 / 1 h / 20 °C 5.1: DIBAL-H / CH2Cl2; hexane / 1 h / -78 °C 5.2: 91 percent / Rochelle's salt / CH2Cl2 / 0.33 h 6.1: 95 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 7.1: 71 percent / MgBr2 / diethyl ether / 5 h / 20 °C 8.1: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C 9.1: aq. HF / acetonitrile / 1.5 h / 20 °C 10.1: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating 11.1: CH2Cl2 / Photolysis 12.1: aq. LiOH / dioxane / 1.5 h / 50 °C 13.1: KMnO4 / H2O; dioxane / 1 h / 40 °C 14.1: aq. HCl View Scheme | |
Multi-step reaction with 14 steps 1.1: 39 percent / methanol / 0 - 20 °C 2.1: 98 percent / porcine liver esterase; aq. Na2HPO4; aq. K2HPO4 / acetone / 3 h / 20 °C / pH 7 3.1: triethylamine / tetrahydrofuran / 0.5 h / 0 °C 3.2: 89 percent / NaBH4 / H2O / 0.5 h / 0 °C 4.1: 93 percent / TsOH monohydrate / CH2Cl2 / 1 h / 20 °C 5.1: DIBAL-H / CH2Cl2; hexane / 1 h / -78 °C 5.2: 91 percent / Rochelle's salt / CH2Cl2 / 0.33 h 6.1: 95 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 7.1: 71 percent / MgBr2 / diethyl ether / 5 h / 20 °C 8.1: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C 9.1: aq. HF / acetonitrile / 1.5 h / 20 °C 10.1: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating 11.1: CH2Cl2 / Photolysis 11.2: toluene / Heating 12.1: aq. LiOH / dioxane / 1.5 h / 50 °C 13.1: KMnO4 / H2O; dioxane / 1 h / 40 °C 14.1: aq. HCl View Scheme |
(+)-byssochlamic acid
Conditions | Yield |
---|---|
Multi-step reaction with 12 steps 1: diethyl ether / 1 h / 0 °C 2: 5.60 g / DBU / CHCl3 / 1 h / Heating 3: 72 percent / aq. LiOH / tetrahydrofuran / 1 h / 0 °C 4: 59 percent / NaI; DIPEA / 1,2-dimethoxy-ethane / 4 h / 20 - 70 °C 5: pig liver esteraze; Na2HPO4; K2HPO4 / acetone / 3 h / 20 °C / pH 7 6: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C 7: aq. HF / acetonitrile / 1.5 h / 20 °C 8: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating 9: CH2Cl2 / Photolysis 10: aq. LiOH / dioxane / 1.5 h / 50 °C 11: KMnO4 / H2O; dioxane / 1 h / 40 °C 12: aq. HCl View Scheme | |
Multi-step reaction with 12 steps 1.1: diethyl ether / 1 h / 0 °C 2.1: 5.60 g / DBU / CHCl3 / 1 h / Heating 3.1: 72 percent / aq. LiOH / tetrahydrofuran / 1 h / 0 °C 4.1: 59 percent / NaI; DIPEA / 1,2-dimethoxy-ethane / 4 h / 20 - 70 °C 5.1: pig liver esteraze; Na2HPO4; K2HPO4 / acetone / 3 h / 20 °C / pH 7 6.1: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C 7.1: aq. HF / acetonitrile / 1.5 h / 20 °C 8.1: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating 9.1: CH2Cl2 / Photolysis 9.2: toluene / Heating 10.1: aq. LiOH / dioxane / 1.5 h / 50 °C 11.1: KMnO4 / H2O; dioxane / 1 h / 40 °C 12.1: aq. HCl View Scheme |
(+)-byssochlamic acid
Conditions | Yield |
---|---|
Multi-step reaction with 11 steps 1: 5.60 g / DBU / CHCl3 / 1 h / Heating 2: 72 percent / aq. LiOH / tetrahydrofuran / 1 h / 0 °C 3: 59 percent / NaI; DIPEA / 1,2-dimethoxy-ethane / 4 h / 20 - 70 °C 4: pig liver esteraze; Na2HPO4; K2HPO4 / acetone / 3 h / 20 °C / pH 7 5: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C 6: aq. HF / acetonitrile / 1.5 h / 20 °C 7: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating 8: CH2Cl2 / Photolysis 9: aq. LiOH / dioxane / 1.5 h / 50 °C 10: KMnO4 / H2O; dioxane / 1 h / 40 °C 11: aq. HCl View Scheme | |
Multi-step reaction with 11 steps 1.1: 5.60 g / DBU / CHCl3 / 1 h / Heating 2.1: 72 percent / aq. LiOH / tetrahydrofuran / 1 h / 0 °C 3.1: 59 percent / NaI; DIPEA / 1,2-dimethoxy-ethane / 4 h / 20 - 70 °C 4.1: pig liver esteraze; Na2HPO4; K2HPO4 / acetone / 3 h / 20 °C / pH 7 5.1: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C 6.1: aq. HF / acetonitrile / 1.5 h / 20 °C 7.1: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating 8.1: CH2Cl2 / Photolysis 8.2: toluene / Heating 9.1: aq. LiOH / dioxane / 1.5 h / 50 °C 10.1: KMnO4 / H2O; dioxane / 1 h / 40 °C 11.1: aq. HCl View Scheme |
methyl (4R)-4-ethyl-2-hydroxymethylcyclopent-1-encarboxylate
(+)-byssochlamic acid
Conditions | Yield |
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Multi-step reaction with 11 steps 1.1: 93 percent / TsOH monohydrate / CH2Cl2 / 1 h / 20 °C 2.1: DIBAL-H / CH2Cl2; hexane / 1 h / -78 °C 2.2: 91 percent / Rochelle's salt / CH2Cl2 / 0.33 h 3.1: 95 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 4.1: 71 percent / MgBr2 / diethyl ether / 5 h / 20 °C 5.1: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C 6.1: aq. HF / acetonitrile / 1.5 h / 20 °C 7.1: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating 8.1: CH2Cl2 / Photolysis 9.1: aq. LiOH / dioxane / 1.5 h / 50 °C 10.1: KMnO4 / H2O; dioxane / 1 h / 40 °C 11.1: aq. HCl View Scheme | |
Multi-step reaction with 11 steps 1.1: 93 percent / TsOH monohydrate / CH2Cl2 / 1 h / 20 °C 2.1: DIBAL-H / CH2Cl2; hexane / 1 h / -78 °C 2.2: 91 percent / Rochelle's salt / CH2Cl2 / 0.33 h 3.1: 95 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 4.1: 71 percent / MgBr2 / diethyl ether / 5 h / 20 °C 5.1: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C 6.1: aq. HF / acetonitrile / 1.5 h / 20 °C 7.1: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating 8.1: CH2Cl2 / Photolysis 8.2: toluene / Heating 9.1: aq. LiOH / dioxane / 1.5 h / 50 °C 10.1: KMnO4 / H2O; dioxane / 1 h / 40 °C 11.1: aq. HCl View Scheme |