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inquiry3-(fur-2-yl)crotonic acid
(S)-2-amino-3-(2-furanyl)propionic acid
Conditions | Yield |
---|---|
With ammonium hydroxide; carbon dioxide; phenylalanine ammonia-lyase at 30℃; for 72h; pH=10.2; | 66% |
D,L-N-acetyl-β-2-furylalanine
(S)-2-amino-3-(2-furanyl)propionic acid
Conditions | Yield |
---|---|
With ammonium hydroxide; cobalt(II) acetate In water at 38℃; acylase I; | 63% |
With porcine kidney acylase 1; cobalt(II) chloride Enzymatic reaction; optical yield given as %ee; enantioselective reaction; |
D,L-N-acetyl-β-2-furylalanine
A
(S)-2-amino-3-(2-furanyl)propionic acid
B
(R)-2-amino-3-(2-furanyl)propionic acid
C
(R)-2-Acetylamino-3-furan-2-yl-propionic acid
Conditions | Yield |
---|---|
With potassium hydroxide; Aspergillus acylase I pH 7.5-8.0; | A 45% B n/a C n/a |
D,L-N-acetyl-β-2-furylalanine
A
(S)-2-amino-3-(2-furanyl)propionic acid
B
(R)-2-Acetylamino-3-furan-2-yl-propionic acid
Conditions | Yield |
---|---|
With potassium hydroxide; potassium phosphate buffer; porcine kidney acylase I at 40℃; relative initial rate of hydrolysis, also with Aspergillus acylase I as a catalyst; with or without CoCl2; |
furfural
(S)-2-amino-3-(2-furanyl)propionic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 91 percent / toluene / 2 h / Heating 2: 90 percent / aq. KOH / 4 h / Heating 3: 66 percent / phenylalanine ammonia-lyase; aq. NH3; CO2 / 72 h / 30 °C / pH 10.2 View Scheme |
ethyl (E)-3-(2-furyl)prop-2-enoate
(S)-2-amino-3-(2-furanyl)propionic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 90 percent / aq. KOH / 4 h / Heating 2: 66 percent / phenylalanine ammonia-lyase; aq. NH3; CO2 / 72 h / 30 °C / pH 10.2 View Scheme |
2-acetylamino-2-(2-furylmethyl)propanedioic acid diethyl ester
(S)-2-amino-3-(2-furanyl)propionic acid
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 82 percent / KOH / ethanol; H2O / 3 h / Ambient temperature 2: 80 percent / dioxane / 39 h / Heating 3: 54 percent / KOH / ethanol; H2O / 17 h / Heating 4: 63 percent / cobalt acetate, 25percent aq. NH4OH / H2O / 38 °C / acylase I View Scheme |
2-acetylamino-3-(2-furyl)propanoic acid ethyl ester
(S)-2-amino-3-(2-furanyl)propionic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 54 percent / KOH / ethanol; H2O / 17 h / Heating 2: 63 percent / cobalt acetate, 25percent aq. NH4OH / H2O / 38 °C / acylase I View Scheme |
2-acetylamino-2-ethoxycarbonyl-3-(2-furyl)propanoic acid
(S)-2-amino-3-(2-furanyl)propionic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 80 percent / dioxane / 39 h / Heating 2: 54 percent / KOH / ethanol; H2O / 17 h / Heating 3: 63 percent / cobalt acetate, 25percent aq. NH4OH / H2O / 38 °C / acylase I View Scheme |
2-bromomethylfuran
(S)-2-amino-3-(2-furanyl)propionic acid
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: sodium methylate / 2 h / Reflux 2: barium(II) hydroxide / 24 h / 20 °C 3: 1,4-dioxane / 24 h / Reflux 4: potassium hydroxide / 17 h / 20 °C 5: porcine kidney acylase 1; cobalt(II) chloride / Enzymatic reaction View Scheme |
C12H15NO6
(S)-2-amino-3-(2-furanyl)propionic acid
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: barium(II) hydroxide / 24 h / 20 °C 2: 1,4-dioxane / 24 h / Reflux 3: potassium hydroxide / 17 h / 20 °C 4: porcine kidney acylase 1; cobalt(II) chloride / Enzymatic reaction View Scheme |
C11H13NO6
(S)-2-amino-3-(2-furanyl)propionic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 1,4-dioxane / 24 h / Reflux 2: potassium hydroxide / 17 h / 20 °C 3: porcine kidney acylase 1; cobalt(II) chloride / Enzymatic reaction View Scheme |
2-Acetylamino-3-furan-2-yl-propionic acid methyl ester
(S)-2-amino-3-(2-furanyl)propionic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: potassium hydroxide / 17 h / 20 °C 2: porcine kidney acylase 1; cobalt(II) chloride / Enzymatic reaction View Scheme |
di-tert-butyl dicarbonate
(S)-2-amino-3-(2-furanyl)propionic acid
(S)-2-t-butoxycarbonylamino-3-furan-2-yl-propionic acid
Conditions | Yield |
---|---|
With triethylamine In methanol at 60℃; for 0.5h; | 100% |
With sodium hydroxide In 1,4-dioxane; water |
methanol
(S)-2-amino-3-(2-furanyl)propionic acid
Conditions | Yield |
---|---|
With thionyl chloride at 0℃; for 5h; Inert atmosphere; Reflux; | 100% |
With acetyl chloride at 0℃; for 18h; Reflux; | 75% |
(S)-2-amino-3-(2-furanyl)propionic acid
benzyl chloroformate
(S)-2-Benzyloxycarbonylamino-3-furan-2-yl-propionic acid
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In tetrahydrofuran at 0 - 20℃; for 2h; | 32% |
(S)-2-amino-3-(2-furanyl)propionic acid
(R)-3-amino-3-(2-furanyl)propionic acid
Conditions | Yield |
---|---|
With phenylalanine aminomutase at 31℃; for 2h; Enzyme kinetics; | |
With Taxus phenylalanine aminomutase enzyme In water; glycerol at 31℃; pH=8; aq. phosphate buffer; Enzymatic reaction; enantioselective reaction; |
(S)-2-amino-3-(2-furanyl)propionic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 1M NaOH / H2O; dioxane 2: DCC / ethyl acetate 3: dimethylformamide View Scheme |
(S)-2-amino-3-(2-furanyl)propionic acid
L-pyroglutamyl-L-furylalanyl-L-prolinamide
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 1M NaOH / H2O; dioxane 2: DCC / ethyl acetate 3: dimethylformamide 4: 1) trifluoroacetic acid, 2) NEt3 / 1) DMF View Scheme |
(S)-2-amino-3-(2-furanyl)propionic acid
N-t-butoxycarbonyl-L-β-2-furylalanine pentafluorophenyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 1M NaOH / H2O; dioxane 2: DCC / ethyl acetate View Scheme |
Conditions | Yield |
---|---|
With thionyl chloride at 70℃; for 4h; |
((S)-(2,6-dichloro-4-methoxyphenyl)(2,4-dichlorophenyl)methyl) N-succinimidyl carbonate
(S)-2-amino-3-(2-furanyl)propionic acid
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In water; acetone | 100 %Spectr. |
((R)-(2,6-dichloro-4-methoxyphenyl)(2,4-dichlorophenyl)methyl) N-succinimidyl carbonate
(S)-2-amino-3-(2-furanyl)propionic acid
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In water; acetone | 100 %Spectr. |
(S)-2-amino-3-(2-furanyl)propionic acid
(rac)-2-amino-3-furan-2-yl-propionic acid
Conditions | Yield |
---|---|
With alanine racemase (accession number AE015451 range 4,245,041-4,246,270), cloned from the genome of Pseudomonas putida (KT2440) In water; glycerol at 31℃; for 1h; aq. phosphate buffer; Enzymatic reaction; |
Conditions | Yield |
---|---|
With triethylamine In N,N-dimethyl-formamide at -78℃; |
Conditions | Yield |
---|---|
With hydrogen; palladium(II) hydroxide In methanol; water under 2068.65 Torr; for 24h; Inert atmosphere; |
(S)-2-amino-3-(2-furanyl)propionic acid
C33H34N2O8
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: toluene-4-sulfonic acid / benzene / 18 h / Reflux 2: 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / tetrahydrofuran / 15 h / 20 °C View Scheme |
(S)-2-amino-3-(2-furanyl)propionic acid
C33H34N2O8
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: toluene-4-sulfonic acid / benzene / 18 h / Reflux 2: 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / tetrahydrofuran / 15 h / 20 °C View Scheme |
(S)-2-amino-3-(2-furanyl)propionic acid
C27H26N2O8
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: toluene-4-sulfonic acid / benzene / 18 h / Reflux 2: 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / tetrahydrofuran / 15 h / 20 °C 3: tetrakis(triphenylphosphine) palladium(0); N-methylaniline / tetrahydrofuran / 1 h / 20 °C View Scheme |
(S)-2-amino-3-(2-furanyl)propionic acid
C27H26N2O8
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: toluene-4-sulfonic acid / benzene / 18 h / Reflux 2: 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / tetrahydrofuran / 15 h / 20 °C 3: tetrakis(triphenylphosphine) palladium(0); N-methylaniline / tetrahydrofuran / 1 h / 20 °C View Scheme |
(S)-2-amino-3-(2-furanyl)propionic acid
γ-L-glutamyl-L-2-furylalanine
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: toluene-4-sulfonic acid / benzene / 18 h / Reflux 2: 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / tetrahydrofuran / 15 h / 20 °C 3: tetrakis(triphenylphosphine) palladium(0); N-methylaniline / tetrahydrofuran / 1 h / 20 °C 4: piperidine / N,N-dimethyl-formamide View Scheme |
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