digitoxigen O-[2'',6''-dideoxy-β-D-ribo-hexopyranosyl]-(1->4)-O-[3'-O-acetyl-2',6'-dideoxy-β-D-ribo-hexopyranosyl]-(1->4)-(3-O-acetyl-2,6-dideoxy-β-D-ribo-hexopyranoside
digitoxin
Conditions | Yield |
---|---|
With lithium hydroxide In methanol; water at 20℃; for 2h; | 83% |
With lithium hydroxide | 83% |
With water; lithium hydroxide In methanol at 20℃; for 3h; | 74% |
With lithium hydroxide |
digitoxin
Conditions | Yield |
---|---|
With biocellulase In water at 37℃; for 48h; | 68% |
(21',23'-epoxy-14'-hydroxy-24'-nor-5'β,14'β-chola-10',22'-dien-3'β-yl) O-<2''',6'''-dideoxy-β-D-ribo-hexopyranosyl>-(1->4)-O-<2'',6''-dideoxy-β-D-ribo-hexopyranosyl>-(1->4)-<2,6-dideoxy-β-D-ribo-hexopyranoside>
digitoxin
Conditions | Yield |
---|---|
With sodium tetrahydroborate; sodium acetate; 3-chloro-benzenecarboperoxoic acid 1.) CH2Cl2, RT, 2 h; 2.) THF/MeOH, 3h, RT; Yield given. Multistep reaction; |
Conditions | Yield |
---|---|
With alkaline saponification |
Digitoxigenin 3-O-bisdigitoxosideacetyldigilanidobioside, or lanatoside A
A
D-Glucose
B
digitoxin
Conditions | Yield |
---|---|
With water; enzyme |
digitoxin
Conditions | Yield |
---|---|
mit Hilfe eines Enzym-Praeparats aus Blaettern von Digitalis purpurea; | |
mit Hilfe eines Enzym-Praeparats aus Blaettern von Digitalis lanata; |
3"',4"'-di-O-acetyl digitoxin
digitoxin
Conditions | Yield |
---|---|
With sodium methylate In methanol | |
With sodium methylate In methanol |
tert-butyl ((2S,6R)-6-methyl-5-oxo-5,6-dihydro-2H-pyran-2-yl) carbonate
digitoxin
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 90 percent / PPh3 / Pd2(DBA)3*CHCl3 / CH2Cl2 / 8 h / 0 °C 2: CeCl3; NaBH4 / methanol / 3 h / -78 °C 3: 89 percent / N-methylmorpholine; Ph3P; diethyl azodicarboxylate / o-nitrobenzenesulfonyl hydrazide / -30 - 20 °C 4: 91 percent / N-methylmorpholine N-oxide; OsO4 / H2O / 3 h / 0 °C 5: 83 percent / LiOH / methanol; H2O / 2 h / 20 °C View Scheme |
digitoxigen 3-O-acetyl-2,6-dideoxy-4-O-((2'R,6'R)-3',6'-dihydro-6'-methyl-2H-pyran-2'-yl)-β-D-ribo-hexopyranoside
digitoxin
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1.1: 91 percent / N-methylmorpholine N-oxide; OsO4 / H2O / 8 h / 0 °C 2.1: p-TsOH / benzene / 20 °C 2.2: 99 percent / p-TsOH / tetrahydrofuran; H2O 3.1: 90 percent / PPh3 / Pd2(DBA)3*CHCl3 / CH2Cl2 / 8 h / 0 °C 4.1: CeCl3; NaBH4 / methanol / 3 h / -78 °C 5.1: 89 percent / N-methylmorpholine; Ph3P; diethyl azodicarboxylate / o-nitrobenzenesulfonyl hydrazide / -30 - 20 °C 6.1: 91 percent / N-methylmorpholine N-oxide; OsO4 / H2O / 3 h / 0 °C 7.1: 83 percent / LiOH / methanol; H2O / 2 h / 20 °C View Scheme |
digitoxin
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1.1: 82 percent / N-methylmorpholine; Ph3P; diethyl azodicarboxylate / o-nitrobenzenesulfonyl hydrazide / 6 h / -30 - 20 °C 2.1: 91 percent / N-methylmorpholine N-oxide; OsO4 / H2O / 8 h / 0 °C 3.1: p-TsOH / benzene / 20 °C 3.2: 99 percent / p-TsOH / tetrahydrofuran; H2O 4.1: 90 percent / PPh3 / Pd2(DBA)3*CHCl3 / CH2Cl2 / 8 h / 0 °C 5.1: CeCl3; NaBH4 / methanol / 3 h / -78 °C 6.1: 89 percent / N-methylmorpholine; Ph3P; diethyl azodicarboxylate / o-nitrobenzenesulfonyl hydrazide / -30 - 20 °C 7.1: 91 percent / N-methylmorpholine N-oxide; OsO4 / H2O / 3 h / 0 °C 8.1: 83 percent / LiOH / methanol; H2O / 2 h / 20 °C View Scheme |
digitoxigen O-[2',6'-dideoxy-β-D-ribo-hexopyranosyl]-(1->4)-(3-O-acetyl-2,6-dideoxy-β-D-ribo-hexopyranoside)
digitoxin
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: p-TsOH / benzene / 20 °C 1.2: 99 percent / p-TsOH / tetrahydrofuran; H2O 2.1: 90 percent / PPh3 / Pd2(DBA)3*CHCl3 / CH2Cl2 / 8 h / 0 °C 3.1: CeCl3; NaBH4 / methanol / 3 h / -78 °C 4.1: 89 percent / N-methylmorpholine; Ph3P; diethyl azodicarboxylate / o-nitrobenzenesulfonyl hydrazide / -30 - 20 °C 5.1: 91 percent / N-methylmorpholine N-oxide; OsO4 / H2O / 3 h / 0 °C 6.1: 83 percent / LiOH / methanol; H2O / 2 h / 20 °C View Scheme |
digitoxigenin 3''-O-acetyl-2'',6''-dideoxy-β-D-ribo-hexopyranosyl-(1->4)-3'-O-acetyl-2',6'-dideoxy-β-D-ribo-hexopyranoside
digitoxin
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 90 percent / PPh3 / Pd2(DBA)3*CHCl3 / CH2Cl2 / 8 h / 0 °C 2: CeCl3; NaBH4 / methanol / 3 h / -78 °C 3: 89 percent / N-methylmorpholine; Ph3P; diethyl azodicarboxylate / o-nitrobenzenesulfonyl hydrazide / -30 - 20 °C 4: 91 percent / N-methylmorpholine N-oxide; OsO4 / H2O / 3 h / 0 °C 5: 83 percent / LiOH / methanol; H2O / 2 h / 20 °C View Scheme |
digitoxigen O-[3'-O-acetyl-2',6'-dideoxy-4'-O-((2''R,6''R)-3'',6''-dihydro-6''-methyl-2H-pyran-2''-yl)-β-D-ribo-hexopyranosyl]-(1->4)-(3-O-acetyl-2,6-dideoxy-β-D-ribo-hexopyranoside)
digitoxin
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 91 percent / N-methylmorpholine N-oxide; OsO4 / H2O / 3 h / 0 °C 2: 83 percent / LiOH / methanol; H2O / 2 h / 20 °C View Scheme | |
Multi-step reaction with 2 steps 1: 91 percent / N-methyl morpholine N-oxide; OsO4 / CH2Cl2; H2O / 4 h 2: 83 percent / LiOH / methanol; H2O / 2 h / 20 °C View Scheme |
digitoxigen O-[3'-O-acetyl-2',6'-dideoxy-4'-O-((2''R,6''R)-5'',6''-dihydro-6''-methyl-5''-hydroxyl-2H-pyran-2''-yl)-β-D-ribo-hexopyranosyl]-(1->4)-(3-O-acetyl-2,6-dideoxy-β-D-ribo-hexopyranoside)
digitoxin
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 89 percent / N-methylmorpholine; Ph3P; diethyl azodicarboxylate / o-nitrobenzenesulfonyl hydrazide / -30 - 20 °C 2: 91 percent / N-methylmorpholine N-oxide; OsO4 / H2O / 3 h / 0 °C 3: 83 percent / LiOH / methanol; H2O / 2 h / 20 °C View Scheme | |
Multi-step reaction with 3 steps 1: 89 percent / N-methyl morpholine; o-nitrobenzenesulfonyl hydrazide; diethylazodicarboxylate / triphenylphosphine / 5 h / -30 - 20 °C 2: 91 percent / N-methyl morpholine N-oxide; OsO4 / CH2Cl2; H2O / 4 h 3: 83 percent / LiOH / methanol; H2O / 2 h / 20 °C View Scheme |
digitoxigen O-[3'-O-acetyl-2',6'-dideoxy-4'-O-((2''R,6''R)-5'',6''-dihydro-6''-methyl-5''-oxo-2H-pyran-2''-yl)-β-D-ribo-hexopyranosyl]-(1->4)-(3-O-acetyl-2,6-dideoxy-β-D-ribo-hexopyranoside)
digitoxin
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: CeCl3; NaBH4 / methanol / 3 h / -78 °C 2: 89 percent / N-methylmorpholine; Ph3P; diethyl azodicarboxylate / o-nitrobenzenesulfonyl hydrazide / -30 - 20 °C 3: 91 percent / N-methylmorpholine N-oxide; OsO4 / H2O / 3 h / 0 °C 4: 83 percent / LiOH / methanol; H2O / 2 h / 20 °C View Scheme |
(5R)-1-hydroxy-5-tert-butyldimethylsilanyloxymethyl-5H-pyran-4-(1H)-one
digitoxin
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: sodium acetate / benzene / 2 h / 80 °C 2: 90 percent / PPh3 / Pd2(DBA)3*CHCl3 / CH2Cl2 / 8 h / 0 °C 3: CeCl3; NaBH4 / methanol / 3 h / -78 °C 4: 89 percent / N-methylmorpholine; Ph3P; diethyl azodicarboxylate / o-nitrobenzenesulfonyl hydrazide / -30 - 20 °C 5: 91 percent / N-methylmorpholine N-oxide; OsO4 / H2O / 3 h / 0 °C 6: 83 percent / LiOH / methanol; H2O / 2 h / 20 °C View Scheme |
3,4-bis-(tert-butyldimethylsilyl)-1,5-anhydro-2,6-dideoxy-D-ribo-hex-1-enitol
digitoxin
Conditions | Yield |
---|---|
Multi-step reaction with 12 steps 1: PPh3; HBr / toluene / 6 h 2: 99 percent / DIBAL / CH2Cl2 / -78 °C 3: 96 percent / DABCO / W(CO)6 / tetrahydrofuran / 65 °C / Irradiation 4: Bu4NF / tetrahydrofuran 5: Et3N; DMAP / CH2Cl2 6: 71 percent / PPh3; HBr / toluene / 6 h 7: 98 percent / DIBAL / CH2Cl2 / -78 °C 8: DABCO / W(CO)6 / tetrahydrofuran / 65 °C / Irradiation 9: Et3N; DMAP / CH2Cl2 10: PPh3; HBr / CHCl3 11: (NH4)HF2; N-methylpyrrolidine / dimethylformamide / 70 °C 12: NaOMe / methanol View Scheme |
(2R,3R,4S)-4-(tert-butyldimethylsiloxy)-hex-5-yne-2,3-diol 2-benzoate ester
digitoxin
Conditions | Yield |
---|---|
Multi-step reaction with 12 steps 1: PPh3; HBr / toluene / 6 h 2: 99 percent / DIBAL / CH2Cl2 / -78 °C 3: 96 percent / DABCO / W(CO)6 / tetrahydrofuran / 65 °C / Irradiation 4: Bu4NF / tetrahydrofuran 5: Et3N; DMAP / CH2Cl2 6: 71 percent / PPh3; HBr / toluene / 6 h 7: 98 percent / DIBAL / CH2Cl2 / -78 °C 8: DABCO / W(CO)6 / tetrahydrofuran / 65 °C / Irradiation 9: Et3N; DMAP / CH2Cl2 10: PPh3; HBr / CHCl3 11: (NH4)HF2; N-methylpyrrolidine / dimethylformamide / 70 °C 12: NaOMe / methanol View Scheme |
4-O-[3,4-bis-(tert-butyldimethylsilyl)-2,6-dideoxy-β-D-allopyranosyl]-3-(tert-butyldimethylsilyl)-1,5-anhydro-2,6-dideoxy-D-ribo-hex-1-entol
digitoxin
Conditions | Yield |
---|---|
Multi-step reaction with 9 steps 1: Bu4NF / tetrahydrofuran 2: Et3N; DMAP / CH2Cl2 3: 71 percent / PPh3; HBr / toluene / 6 h 4: 98 percent / DIBAL / CH2Cl2 / -78 °C 5: DABCO / W(CO)6 / tetrahydrofuran / 65 °C / Irradiation 6: Et3N; DMAP / CH2Cl2 7: PPh3; HBr / CHCl3 8: (NH4)HF2; N-methylpyrrolidine / dimethylformamide / 70 °C 9: NaOMe / methanol View Scheme |
(2R,3R,4S)-3-[(2S,4S,5R,6R)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-4-(tert-butyl-dimethyl-silanyloxy)-hex-5-yn-2-ol
digitoxin
Conditions | Yield |
---|---|
Multi-step reaction with 10 steps 1: 96 percent / DABCO / W(CO)6 / tetrahydrofuran / 65 °C / Irradiation 2: Bu4NF / tetrahydrofuran 3: Et3N; DMAP / CH2Cl2 4: 71 percent / PPh3; HBr / toluene / 6 h 5: 98 percent / DIBAL / CH2Cl2 / -78 °C 6: DABCO / W(CO)6 / tetrahydrofuran / 65 °C / Irradiation 7: Et3N; DMAP / CH2Cl2 8: PPh3; HBr / CHCl3 9: (NH4)HF2; N-methylpyrrolidine / dimethylformamide / 70 °C 10: NaOMe / methanol View Scheme |
Benzoic acid (1R,2R,3S)-2-[(2S,4S,5R,6R)-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-3-(tert-butyl-dimethyl-silanyloxy)-1-methyl-pent-4-ynyl ester
digitoxin
Conditions | Yield |
---|---|
Multi-step reaction with 11 steps 1: 99 percent / DIBAL / CH2Cl2 / -78 °C 2: 96 percent / DABCO / W(CO)6 / tetrahydrofuran / 65 °C / Irradiation 3: Bu4NF / tetrahydrofuran 4: Et3N; DMAP / CH2Cl2 5: 71 percent / PPh3; HBr / toluene / 6 h 6: 98 percent / DIBAL / CH2Cl2 / -78 °C 7: DABCO / W(CO)6 / tetrahydrofuran / 65 °C / Irradiation 8: Et3N; DMAP / CH2Cl2 9: PPh3; HBr / CHCl3 10: (NH4)HF2; N-methylpyrrolidine / dimethylformamide / 70 °C 11: NaOMe / methanol View Scheme |
digitoxin
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1: Et3N; DMAP / CH2Cl2 2: 71 percent / PPh3; HBr / toluene / 6 h 3: 98 percent / DIBAL / CH2Cl2 / -78 °C 4: DABCO / W(CO)6 / tetrahydrofuran / 65 °C / Irradiation 5: Et3N; DMAP / CH2Cl2 6: PPh3; HBr / CHCl3 7: (NH4)HF2; N-methylpyrrolidine / dimethylformamide / 70 °C 8: NaOMe / methanol View Scheme |
Acetic acid (2R,3R,4S,6S)-3-acetoxy-6-[(2R,3R,4S)-4-(tert-butyl-dimethyl-silanyloxy)-2-methyl-3,4-dihydro-2H-pyran-3-yloxy]-2-methyl-tetrahydro-pyran-4-yl ester
digitoxin
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: 71 percent / PPh3; HBr / toluene / 6 h 2: 98 percent / DIBAL / CH2Cl2 / -78 °C 3: DABCO / W(CO)6 / tetrahydrofuran / 65 °C / Irradiation 4: Et3N; DMAP / CH2Cl2 5: PPh3; HBr / CHCl3 6: (NH4)HF2; N-methylpyrrolidine / dimethylformamide / 70 °C 7: NaOMe / methanol View Scheme |
(2R,3S,4S,6S)-6-{(2R,3R,4S,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[(2R,3R,4S)-4-(tert-butyl-dimethyl-silanyloxy)-2-methyl-3,4-dihydro-2H-pyran-3-yloxy]-2-methyl-tetrahydro-pyran-3-yloxy}-2-methyl-tetrahydro-pyran-3,4-diol
digitoxin
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: Et3N; DMAP / CH2Cl2 2: PPh3; HBr / CHCl3 3: (NH4)HF2; N-methylpyrrolidine / dimethylformamide / 70 °C 4: NaOMe / methanol View Scheme |
digitoxin
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: DABCO / W(CO)6 / tetrahydrofuran / 65 °C / Irradiation 2: Et3N; DMAP / CH2Cl2 3: PPh3; HBr / CHCl3 4: (NH4)HF2; N-methylpyrrolidine / dimethylformamide / 70 °C 5: NaOMe / methanol View Scheme |
Acetic acid (2R,3R,4S,6S)-3-acetoxy-6-{(2R,3R,4S,6S)-4-(tert-butyl-dimethyl-silanyloxy)-6-[(2R,3R,4S)-4-(tert-butyl-dimethyl-silanyloxy)-2-methyl-3,4-dihydro-2H-pyran-3-yloxy]-2-methyl-tetrahydro-pyran-3-yloxy}-2-methyl-tetrahydro-pyran-4-yl ester
digitoxin
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: PPh3; HBr / CHCl3 2: (NH4)HF2; N-methylpyrrolidine / dimethylformamide / 70 °C 3: NaOMe / methanol View Scheme |
Benzoic acid (1R,2R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-2-[(2S,4S,5R,6R)-4-(tert-butyl-dimethyl-silanyloxy)-5-((2S,4S,5R,6R)-4,5-diacetoxy-6-methyl-tetrahydro-pyran-2-yloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-1-methyl-pent-4-ynyl ester
digitoxin
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: 98 percent / DIBAL / CH2Cl2 / -78 °C 2: DABCO / W(CO)6 / tetrahydrofuran / 65 °C / Irradiation 3: Et3N; DMAP / CH2Cl2 4: PPh3; HBr / CHCl3 5: (NH4)HF2; N-methylpyrrolidine / dimethylformamide / 70 °C 6: NaOMe / methanol View Scheme |
C57H96O15Si2
digitoxin
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: (NH4)HF2; N-methylpyrrolidine / dimethylformamide / 70 °C 2: NaOMe / methanol View Scheme |
phenyl 3-O-benzyl-4-O-tert-butyldimethylsilyl-2,6-dideoxy-β-D-ribohexapyranosyl-(1→4)-3-O-benzyl-2,6-dideoxy-β-D-ribo-hexapyranosyl-(1→4)-3-O-benzyl-6-deoxy-2-O-methyl-1-thio-α-D-ribohexopyranoside
A
C1′-epi-digitoxin
B
digitoxin
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: lithium 4,4′-di(tert-butyl)biphenyl / tetrahydrofuran / 0.25 h / -20 °C 2: 1H-imidazole / N,N-dimethyl-formamide / 40 h / 20 - 50 °C 3: triphenylphosphine hydrobromide / chloroform / 24 h / 20 °C / Molecular sieve 4: ammonium fluoride-hydrogen fluoride / N,N-dimethyl-formamide; 1-methyl-pyrrolidin-2-one / 144 h / 80 °C View Scheme | |
Multi-step reaction with 5 steps 1: tetrabutyl ammonium fluoride / tetrahydrofuran / 5 h / 40 °C 2: lithium 4,4′-di(tert-butyl)biphenyl / tetrahydrofuran / 0.25 h / -20 °C 3: 1H-imidazole / N,N-dimethyl-formamide / 0.75 h / 20 °C 4: triphenylphosphine hydrobromide / chloroform / 3.17 h / 20 °C / Molecular sieve 5: ammonium fluoride-hydrogen fluoride / N,N-dimethyl-formamide; 1-methyl-pyrrolidin-2-one / 4 h / 70 °C View Scheme |
Conditions | Yield |
---|---|
Stage #1: digitoxin With 2,4,6-trimethyl-pyridine; (2S,5S)-2,5-bis[[(2S)-3-(1H-indol-3-yl)-1-(octyloxy)-1-oxopropan-2-ylamino]carbonyl]-1-(pyridin-4-yl)pyrrolidine In chloroform at 20℃; for 0.166667h; Stage #2: acetic anhydride In chloroform at 20℃; for 24h; regioselective reaction; | 98% |
Conditions | Yield |
---|---|
Stage #1: digitoxin With 2,4,6-trimethyl-pyridine; (2S,5S)-2,5-bis[[(2S)-3-(1H-indol-3-yl)-1-(octyloxy)-1-oxopropan-2-ylamino]carbonyl]-1-(pyridin-4-yl)pyrrolidine In chloroform at 20℃; for 0.166667h; Stage #2: 2-Methylpropionic anhydride In chloroform at 20℃; for 24h; regioselective reaction; | 98% |
Conditions | Yield |
---|---|
Stage #1: digitoxin With 2,4,6-trimethyl-pyridine; (2S,5S)-2,5-bis[[(2S)-3-(1H-indol-3-yl)-1-(octyloxy)-1-oxopropan-2-ylamino]carbonyl]-1-(pyridin-4-yl)pyrrolidine In chloroform at 20℃; for 0.166667h; Stage #2: docosanoic acid anhydride In chloroform at 20℃; for 24h; regioselective reaction; | 96% |
Conditions | Yield |
---|---|
With sulfuric acid In methanol at 0℃; for 5h; | 95% |
With toluene-4-sulfonic acid In methanol at 20℃; | 79% |
With hydrogenchloride; ethanol; water |
thiophen-2-carboxylic anhydride
digitoxin
digitoxin 4"'-(thiophene-2-carboxylate)
Conditions | Yield |
---|---|
Stage #1: digitoxin With 2,4,6-trimethyl-pyridine; (2S,5S)-2,5-bis[[(2S)-3-(1H-indol-3-yl)-1-(octyloxy)-1-oxopropan-2-ylamino]carbonyl]-1-(pyridin-4-yl)pyrrolidine In chloroform at 20℃; for 0.166667h; Stage #2: thiophen-2-carboxylic anhydride In chloroform at 20℃; for 24h; regioselective reaction; | 94% |
Conditions | Yield |
---|---|
Stage #1: digitoxin With 2,4,6-trimethyl-pyridine; (2S,5S)-2,5-bis[[(2S)-3-(1H-indol-3-yl)-1-(octyloxy)-1-oxopropan-2-ylamino]carbonyl]-1-(pyridin-4-yl)pyrrolidine In chloroform at 20℃; for 0.166667h; Stage #2: β-furan carboxylic anhydride In chloroform at 20℃; for 24h; regioselective reaction; | 93% |
Conditions | Yield |
---|---|
Stage #1: digitoxin With 2,4,6-trimethyl-pyridine; (2S,5S)-2,5-bis[[(2S)-3-(1H-indol-3-yl)-1-(octyloxy)-1-oxopropan-2-ylamino]carbonyl]-1-(pyridin-4-yl)pyrrolidine In chloroform at 20℃; for 0.166667h; Stage #2: lauric anhydride In chloroform at 20℃; for 24h; regioselective reaction; | 92% |
digitoxin
digitoxigen O-[2',6'-dideoxy-β-D-ribo-hexopyranosyl]-(1->4)-(2,6-dideoxy-β-D-ribo-hexopyranoside)
Conditions | Yield |
---|---|
Stage #1: digitoxin With sodium periodate In ethanol; water Stage #2: With sodium tetrahydroborate; ethanol for 4h; Stage #3: With hydrogenchloride In methanol; water | 90% |
With hydrogenchloride |
Conditions | Yield |
---|---|
Stage #1: digitoxin With 2,4,6-trimethyl-pyridine; (2S,5S)-2,5-bis[[(2S)-3-(1H-indol-3-yl)-1-(octyloxy)-1-oxopropan-2-ylamino]carbonyl]-1-(pyridin-4-yl)pyrrolidine In chloroform at 20℃; for 0.166667h; Stage #2: palmitic anhydride In chloroform at 20℃; for 24h; regioselective reaction; | 90% |
Conditions | Yield |
---|---|
Stage #1: digitoxin With 2,4,6-trimethyl-pyridine; (2S,5S)-2,5-bis[[(2S)-3-(1H-indol-3-yl)-1-(octyloxy)-1-oxopropan-2-ylamino]carbonyl]-1-(pyridin-4-yl)pyrrolidine In chloroform at 20℃; for 0.166667h; Stage #2: cinnamic anhydride In chloroform at 20℃; for 24h; regioselective reaction; | 90% |
Conditions | Yield |
---|---|
Stage #1: digitoxin With 2,4,6-trimethyl-pyridine; (2S,5S)-2,5-bis[[(2S)-3-(1H-indol-3-yl)-1-(octyloxy)-1-oxopropan-2-ylamino]carbonyl]-1-(pyridin-4-yl)pyrrolidine In chloroform at 20℃; for 0.166667h; Stage #2: 4-pentenoic anhydride In chloroform at 20℃; for 24h; regioselective reaction; | 90% |
Conditions | Yield |
---|---|
Stage #1: digitoxin With 2,4,6-trimethyl-pyridine; (2S,5S)-2,5-bis[[(2S)-3-(1H-indol-3-yl)-1-(octyloxy)-1-oxopropan-2-ylamino]carbonyl]-1-(pyridin-4-yl)pyrrolidine In chloroform at 20℃; for 0.166667h; Stage #2: benzoic acid anhydride In chloroform at 20℃; for 24h; regioselective reaction; | 90% |
digitoxin
(21',23'-epoxy-14'-hydroxy-24'-nor-5'β,14'β-chola-10',22'-dien-3'β-yl) O-<2''',6'''-dideoxy-β-D-ribo-hexopyranosyl>-(1->4)-O-<2'',6''-dideoxy-β-D-ribo-hexopyranosyl>-(1->4)-<2,6-dideoxy-β-D-ribo-hexopyranoside>
Conditions | Yield |
---|---|
86% | |
With diisobutylaluminium hydride In tetrahydrofuran at -70℃; for 1h; | 86% |
2-Methylpropionic anhydride
digitoxin
A
4"'-O-isobutyryl digitoxin
B
3"',4"'-O-di-isobutyryl digitoxin
Conditions | Yield |
---|---|
Stage #1: digitoxin With 2,4,6-trimethyl-pyridine; dmap In chloroform at -20℃; for 0.166667h; Stage #2: 2-Methylpropionic anhydride In chloroform at -20℃; for 24h; regioselective reaction; | A 80% B 10% |
digitoxin
2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide
digitoxigen (2,3,4,6-tetraacetyl-β-D-glucopyranosyl)-(1→4)-(2,6-dideoxy-β-D-ribohexopyranosyl)-(1→4)-(2,6-dideoxy-β-D-ribohexopyranosyl)-(1→4)-2,6-dideoxy-β-D-ribohexopyranoside
Conditions | Yield |
---|---|
With diphenylborate ethanolamine ester; silver(l) oxide In dichloromethane at 20℃; for 20h; Reagent/catalyst; regioselective reaction; | 77% |
Conditions | Yield |
---|---|
With Jones reagent In acetone at 0 - 20℃; for 3h; Jones oxidation; | 75% |
Multi-step reaction with 2 steps 1: H2O 2: 15 g / CrO3; pyridine / CHCl3 / 10 h / 20 °C View Scheme | |
With chromium(VI) oxide; sulfuric acid In acetone | |
With chromium(VI) oxide; sulfuric acid; water In acetone |
digitoxin
acetobromocellobiose
digitoxigen (2,3,4,6-tetracetyl-β-D-glucopyranosyl)-(1→4)-(2,3,6-triacetyl-β-D-glucopyranosyl)-(1→4)-(2,6-dideoxy-β-D-ribohexopyranosyl)-(1→4)-2,6-dideoxy-β-D-hexopyranosyl-(1→4)-2,6-dideoxy-β-D-ribohexopyranoside
Conditions | Yield |
---|---|
With diphenylborate ethanolamine ester; silver(l) oxide In dichloromethane at 20℃; for 20h; regioselective reaction; | 74% |
digitoxin
4-((3S,5R,8R,10S,13R,14S,17R)-14-hydroxy-3-(((2R,4S,5S,6R)-4-hydroxy-5-(((2S,4S,5S,6R)-4-hydroxy-5-(((2S,4S,5R,6R)-5-hydroxy-6-methyl-4-(((R)-1-phenylprop-2-yn-1-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-6-methyltetrahydro-2H-pyran-2-yl)oxy)-6-methyltetrahydro-2H-pyran-2-yl)oxy)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)furan-2(5H)-one
Conditions | Yield |
---|---|
With 2,6-bis[(4S)-4-methyl-4,5-dihydrooxazol-2-yl]pyridine; tetrakis(acetonitrile)copper(I)tetrafluoroborate; triethylamine; 10-hydroxy-4a,10a-dihydrobenzo[b][1,4]benzoxaborinine In tetrahydrofuran at -20℃; for 24h; | 74% |
digitoxin
4-((3S,5R,8R,10S,13R,14S,17R)-14-hydroxy-3-(((2R,4S,5S,6R)-4-hydroxy-5-(((2S,4S,5S,6R)-4-hydroxy-5-(((2S,4S,5S,6R)-4-hydroxy-6-methyl-5-(((S)-1-phenylprop-2-yn-1-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-6-methyltetrahydro-2H-pyran-2-yl)oxy)-6-methyltetrahydro-2H-pyran-2-yl)oxy)-10,13-dimethylhexadecahydro-1Hcyclopenta[a]phenanthren-17-yl)furan-2(5H)-one
Conditions | Yield |
---|---|
With tetrakis(acetonitrile)copper(I)tetrafluoroborate; R,R-C5H3N(C3H3NOPh)2; triethylamine; 10-hydroxy-4a,10a-dihydrobenzo[b][1,4]benzoxaborinine In tetrahydrofuran at -20℃; for 24h; | 70% |
digitoxin
4-((3S,5R,8R,10S,13R,14S,17R)-3-(((2R,4S,5S,6R)-5-(((2S,4S,5S,6R)-5-(((2S,4S,5S,6R)-5-(((R)-5-(4-benzoylphenoxy)pent-1-yn-3-yl)oxy)-4-hydroxy-6-methyltetrahydro-2Hpyran-2-yl)oxy)-4-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-14-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)furan-2(5H)-one
Conditions | Yield |
---|---|
With tetrakis(acetonitrile)copper(I)tetrafluoroborate; R,R-C5H3N(C3H3NOPh)2; triethylamine; 10-hydroxy-4a,10a-dihydrobenzo[b][1,4]benzoxaborinine In tetrahydrofuran at 20℃; for 24h; Molecular sieve; | 68% |
acetic anhydride
digitoxin
A
3"',4"'-di-O-acetyl digitoxin
B
4"'-O-acetyl digitoxin
Conditions | Yield |
---|---|
Stage #1: digitoxin With 2,4,6-trimethyl-pyridine; dmap In chloroform at 20℃; for 0.166667h; Stage #2: acetic anhydride In chloroform at 20℃; for 24h; regioselective reaction; | A 18% B 66% |
digitoxin
2,3,6,2',3',4',6'-hepta-O-acetyl-lactosyl bromide
digitoxigen (2,3,4,6-tetracetyl-β-D-galactopyranosyl)-(1→4)-(2,3,6-triacetyl-β-D-glucopyranosyl)-(1→4)-(2,6-dideoxy-β-D-ribohexopyranosyl)-(1→4)-2,6-dideoxy-β-D-hexopyranosyl-(1→4)-2,6-dideoxy-β-D-ribohexopyranoside
Conditions | Yield |
---|---|
With diphenylborate ethanolamine ester; silver(l) oxide In dichloromethane at 20℃; for 20h; regioselective reaction; | 64% |
Conditions | Yield |
---|---|
With diphenylborate ethanolamine ester; silver(l) oxide In dichloromethane at 20℃; for 20h; regioselective reaction; | 63% |
2,3,4-tri-O-acetyl-α-L-fucopyranosyl bromide
digitoxin
digitoxigen (2,3,4,6-triacetyl-β-L-fucopyranosyl)-(1→4)-(2,6-dideoxy-β-D-ribohexopyranosyl)-(1→4)-(2,6-dideoxy-β-D-ribohexopyranosyl)-(1→4)-2,6-dideoxy-β-D-ribohexopyranoside
Conditions | Yield |
---|---|
With diphenylborate ethanolamine ester; silver(l) oxide In dichloromethane at 20℃; for 20h; regioselective reaction; | 51% |
digitoxin
21-hydroxyiminodigitoxin
Conditions | Yield |
---|---|
With hydrogenchloride; sodium nitrite In methanol | 17% |
digitoxin
3β-
Conditions | Yield |
---|---|
for 96h; Irradiation; | 7.5% |
Conditions | Yield |
---|---|
With acetic anhydride |
acetic anhydride
digitoxin
14-hydroxy-3β-(tetra-O-acetyl-lin-tri[1β=>4]-D-ribo-2,6-dideoxy-hexopyranosyloxy)-5β,14β-card-20(22)-enolide
Conditions | Yield |
---|---|
With pyridine | |
In pyridine at 85℃; for 5h; | 590 mg |
The IUPAC name of Digitoxin is 3-[(3S,5R,8R,9S,10S,13R,14S,17R)-3-[(2R,4S,5S,6R)-5-[(2S,4S,5S,6R)-5-[(2S,4S,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy-4-hydroxy-6-methyloxan-2-yl]oxy-4-hydroxy-6-methyloxan-2-yl]oxy-14-hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one. With the CAS registry number 71-63-6, it is also named as Acedoxin. The product's categories are Biochemistry; Glycosides; Steroidglycosides; Steroids; Sugars; Intermediates & Fine Chemicals; Pharmaceuticals; AT Pase, and the other registry numbers are 1339-93-1; 1367-39-1; 1391-34-0; 82476-56-0. Besides, it is odorless white or pale buff microcrystalline powder, which should be sealed in brown glass bottle and stored in a dark, dry place. In addition, its molecular formula is C41H64O13 and molecular weight is 764.94.
The other characteristics of this product can be summarized as: (1)EINECS: 200-760-5; (2)ACD/LogP: 2.44; (3)# of Rule of 5 Violations: 3; (4)ACD/LogD (pH 5.5): 2.44; (5)ACD/LogD (pH 7.4): 2.44; (6)ACD/BCF (pH 5.5): 41.88; (7)ACD/BCF (pH 7.4): 41.88; (8)ACD/KOC (pH 5.5): 504.28; (9)ACD/KOC (pH 7.4): 504.28; (10)#H bond acceptors: 13; (11)#H bond donors: 5; (12)#Freely Rotating Bonds: 12; (13)Index of Refraction: 1.593; (14)Molar Refractivity: 194.87 cm3; (15)Molar Volume: 574.5 cm3; (16)Surface Tension: 61.2 dyne/cm; (17)Density: 1.33 g/cm3; (18)Flash Point: 269.5 °C; (19)Melting Point: 240 °C; (20)Enthalpy of Vaporization: 148.93 kJ/mol; (21)Boiling Point: 902.3 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25 °C.
Preparation and Uses of Digitoxin: this chemical can be extract from digitalis leaf. Additionally, as this chemical can enhance myocardial contractility, slower heart rate and inhibit conduction, it is used as a cardiotonic drug.
When you are using this chemical, please be cautious about it as the following: it is toxic by inhalation and if swallowed. And it is danger of cumulative effects. In case of accident or if you feel unwell, please seek medical advice immediately (show the label whenever possible.)
People can use the following data to convert to the molecule structure.
(1)SMILES: O=C\1OC/C(=C/1)[C@H]2CC[C@@]8(O)[C@]2(C)CC[C@H]7[C@H]8CC[C@H]6[C@]7(C)CC[C@H](O[C@@H]5O[C@H](C)[C@@H](O[C@@H]4O[C@@H]([C@@H](O[C@@H]3O[C@@H]([C@@H](O)[C@@H](O)C3)C)[C@@H](O)C4)C)[C@@H](O)C5)C6
(2)InChI: InChI=1/C41H64O13/c1-20-36(46)29(42)16-34(49-20)53-38-22(3)51-35(18-31(38)44)54-37-21(2)50-33(17-30(37)43)52-25-8-11-39(4)24(15-25)6-7-28-27(39)9-12-40(5)26(10-13-41(28,40)47)23-14-32(45)48-19-23/h14,20-22,24-31,33-38,42-44,46-47H,6-13,15-19H2,1-5H3/t20-,21-,22-,24-,25+,26-,27+,28-,29+,30+,31+,33+,34+,35+,36-,37-,38-,39+,40-,41+/m1/s1
(3)InChIKey: WDJUZGPOPHTGOT-XUDUSOBPBI
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
cat | LD50 | intraperitoneal | 170ug/kg (0.17mg/kg) | Archives Internationales de Pharmacodynamie et de Therapie. Vol. 155, Pg. 165, 1965. | |
cat | LD50 | oral | 180ug/kg (0.18mg/kg) | Archives Internationales de Pharmacodynamie et de Therapie. Vol. 159, Pg. 1, 1966. | |
cat | LDLo | intraarterial | 440ug/kg (0.44mg/kg) | Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 141, Pg. 329, 1929. | |
cat | LDLo | intraduodenal | 315ug/kg (0.315mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 20, Pg. 1765, 1970. | |
cat | LDLo | intravenous | 180ug/kg (0.18mg/kg) | Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 184, Pg. 181, 1937. | |
cat | LDLo | unreported | 325mg/kg (325mg/kg) | "Die Herzwirksamen Glykoside," Baumgarten, G., and W. Forster, Leipzig, Ger. Dem. Rep., VEB Georg Thieme, 1963Vol. -, Pg. 33, 1963. | |
dog | LDLo | intravenous | 500ug/kg (0.5mg/kg) | "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1343, 1935. | |
frog | LD50 | intravenous | 730ug/kg (0.73mg/kg) | Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 61, Pg. 231, 1965. | |
frog | LD50 | oral | 3050ug/kg (3.05mg/kg) | Japanese Journal of Pharmacology. Vol. 9, Pg. 91, 1960. | |
frog | LD50 | subcutaneous | 1050ug/kg (1.05mg/kg) | Japanese Journal of Pharmacology. Vol. 9, Pg. 91, 1960. | |
frog | LDLo | parenteral | 1mg/kg (1mg/kg) | Chemical and Pharmaceutical Bulletin. Vol. 11, Pg. 613, 1963. | |
guinea pig | LD50 | intraduodenal | 3mg/kg (3mg/kg) | CARDIAC: CARDIOMYOPATHY INCLUDING INFARCTION CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION) | Arzneimittel-Forschung. Drug Research. Vol. 21, Pg. 225, 1971. |
guinea pig | LD50 | intraperitoneal | 1800ug/kg (1.8mg/kg) | Archives Internationales de Pharmacodynamie et de Therapie. Vol. 242, Pg. 35, 1979. | |
guinea pig | LD50 | oral | 3700ug/kg (3.7mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 8, Pg. 557, 1958. | |
guinea pig | LDLo | intraduodenal | 7250ug/kg (7.25mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 20, Pg. 229, 1970. | |
guinea pig | LDLo | intravenous | 310ug/kg (0.31mg/kg) | Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 237, Pg. 222, 1959. | |
infant | TDLo | oral | 150ug/kg (0.15mg/kg) | CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION) GASTROINTESTINAL: NAUSEA OR VOMITING | American Journal of Diseases of Children. Vol. 130, Pg. 425, 1976. |
infant | TDLo | parenteral | 270ug/kg/1D-I (0.27mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION) CARDIAC: EKG CHANGES NOT DIAGNOSTIC OF ABOVE | Indian Pediatrics. Vol. 30, Pg. 81, 1993. |
man | LDLo | oral | 286ug/kg (0.286mg/kg) | PERIPHERAL NERVE AND SENSATION: PARESTHESIS CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP BLOOD: THROMBOCYTOPENIA | Clinical Toxicology. Vol. 18, Pg. 679, 1981. |
man | LDLo | unreported | 44ug/kg (0.044mg/kg) | "Poisoning; Toxicology, Symptoms, Treatments," 2nd ed., Arena, J.M., Springfield, IL, C.C. Thomas, 1970Vol. 2, Pg. 73, 1970. | |
man | TDLo | oral | 71ug/kg (0.071mg/kg) | CARDIAC: CARDIOMYOPATHY INCLUDING INFARCTION CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION) | American Journal of Emergency Medicine. Vol. 2, Pg. 504, 1984. |
mouse | LD50 | intracrebral | 49ug/kg (0.049mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | Arzneimittel-Forschung. Drug Research. Vol. 11, Pg. 908, 1961. |
mouse | LD50 | intraperitoneal | 3900ug/kg (3.9mg/kg) | Archives Internationales de Pharmacodynamie et de Therapie. Vol. 155, Pg. 165, 1965. | |
mouse | LD50 | intravenous | 4100ug/kg (4.1mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 8, Pg. 557, 1958. | |
mouse | LD50 | oral | 4950ug/kg (4.95mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 8, Pg. 557, 1958. | |
mouse | LD50 | subcutaneous | 22180ug/kg (22.18mg/kg) | BRAIN AND COVERINGS: RECORDINGS FROM SPECIFIC AREAS OF CNS BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD CARDIAC: OTHER CHANGES | Archives Internationales de Pharmacodynamie et de Therapie. Vol. 153, Pg. 436, 1965. |
pig | LDLo | intraduodenal | 550ug/kg (0.55mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 20, Pg. 229, 1970. | |
pig | LDLo | intravenous | 400ug/kg (0.4mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 20, Pg. 229, 1970. | |
pigeon | LD50 | intraperitoneal | 320ug/kg (0.32mg/kg) | Journal of Pharmacy and Pharmacology. Vol. 14, Pg. 96, 1962. | |
pigeon | LDLo | intravenous | 443ug/kg (0.443mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 21, Pg. 225, 1971. | |
pigeon | LDLo | parenteral | 600ug/kg (0.6mg/kg) | Chemical and Pharmaceutical Bulletin. Vol. 11, Pg. 613, 1963. | |
rabbit | LDLo | intravenous | 1mg/kg (1mg/kg) | "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1343, 1935. | |
rat | LD50 | intravenous | 3900ug/kg (3.9mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | Arzneimittel-Forschung. Drug Research. Vol. 11, Pg. 848, 1961. |
rat | LD50 | oral | 23750ug/kg (23.75mg/kg) | Archives Internationales de Pharmacodynamie et de Therapie. Vol. 164, Pg. 47, 1966. | |
rat | LD50 | subcutaneous | 16430ug/kg (16.43mg/kg) | Archives Internationales de Pharmacodynamie et de Therapie. Vol. 164, Pg. 47, 1966. | |
women | TDLo | oral | 300ug/kg (0.3mg/kg) | CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION) | American Journal of Emergency Medicine. Vol. 2, Pg. 504, 1984. |
women | TDLo | oral | 400ug/kg (0.4mg/kg) | CARDIAC: EKG CHANGES NOT DIAGNOSTIC OF ABOVE GASTROINTESTINAL: NAUSEA OR VOMITING | Clinical Toxicology. Vol. 18, Pg. 679, 1981. |
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