(S)-(-)-β-methyl-β-propiolactone
(S)-3-Hydroxybutanoic Acid
Conditions | Yield |
---|---|
With sodium hydroxide In water at 0℃; for 0.333333h; | 71% |
With hydrogenchloride In diethyl ether; water for 18h; pH=2; | 63% |
(S)-3-hydroxybutyric acid methyl ester
(S)-3-Hydroxybutanoic Acid
Conditions | Yield |
---|---|
With sodium hydroxide In water for 36h; | 53% |
With water; potassium hydroxide at 0 - 20℃; for 32h; | 50% |
With potassium hydroxide In ethanol at 25℃; for 48h; | |
With potassium hydroxide | |
With potassium hydroxide at 20℃; for 72h; |
(S)-(-)-β-methyl-β-propiolactone
A
(S)-3-Hydroxybutanoic Acid
B
(R)-3-Mercaptobuttersaeure
Conditions | Yield |
---|---|
With sodium hydrogensulfide In water 0 deg C, 1 h, then room temp., 24 h; Yields of byproduct given; | A n/a B 47% |
Conditions | Yield |
---|---|
With Rhodococcus erythropolis SET1 cells In aq. phosphate buffer at 25℃; for 24h; pH=7; Microbiological reaction; enantioselective reaction; | 42% |
With hydrogenchloride | |
With bacterial isolate In aq. phosphate buffer at 15℃; pH=7.2; | n/a |
1.3-butanediol
A
1,3-butanediol
B
(S)-3-Hydroxybutanoic Acid
Conditions | Yield |
---|---|
With phosphate buffer at 30℃; for 24h; Candida boidinii KK912 (IFO 10574); | A 32% B 13% |
Conditions | Yield |
---|---|
With cis-nitrous acid nachfolgend Verseifen; |
Conditions | Yield |
---|---|
With cis-nitrous acid nachfolgend Verseifen; |
Conditions | Yield |
---|---|
bei der Einw. von Bact. ascendens; |
Conditions | Yield |
---|---|
bei der Reduktion durch gaerende Hefe; | |
durch ein stereospezifisches Enzym aus Schweinenieren-Extrakt; |
3-Hydroxybutyric acid
(S)-3-Hydroxybutanoic Acid
Conditions | Yield |
---|---|
Man laesst auf der Ammoniumsalzloesung Aspergillus griseus wachsen; |
1.3-butanediol
A
(S)-3-Hydroxybutanoic Acid
B
(R)-3-hydroxybutyric acid
C
2-acetoacetic acid
Conditions | Yield |
---|---|
With D-glucose; calcium carbonate at 27℃; for 48h; Hansenula anomala IFO 0195; Yield given. Yields of byproduct given. Title compound not separated from byproducts; | |
With D-glucose; calcium carbonate at 27℃; for 48h; Product distribution; Hansenula anomala IFO 0195, potato-dextrose-agar; other yeasts, influence of glucose, fructose, temperature: stereoselectivity; also with optically active 1,3-butanediol; |
2-acetoacetic acid
A
(S)-3-Hydroxybutanoic Acid
B
(R)-3-hydroxybutyric acid
Conditions | Yield |
---|---|
With potassium dihydrogenphosphate; baker's yeast; D-glucose In water at 28℃; for 9h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; | |
With potassium dihydrogenphosphate; baker's yeast; D-glucose In water at 28℃; for 9h; Product distribution; other times; other β-keto acids investigated; | |
With diisopinocampheylborane In tetrahydrofuran at 20℃; for 32h; Title compound not separated from byproducts.; |
ethyl (S)-3-hydroxybutyrate
(S)-3-Hydroxybutanoic Acid
Conditions | Yield |
---|---|
With potassium hydroxide for 12h; Ambient temperature; | |
With Candida antarctica lipase B; 4-nitro-phenol; MOPS buffer In water at 25℃; pH=7.2; Enzyme kinetics; Further Variations:; Reagents; Enzymatic reaction; |
ethyl acetoacetate
A
(S)-3-Hydroxybutanoic Acid
B
(R)-3-hydroxybutyric acid
C
Ethyl (R)-3-hydroxybutanoate
D
ethyl (S)-3-hydroxybutyrate
Conditions | Yield |
---|---|
With Halobacterium halobium; pepton; potassium chloride; water; sodium citrate; magnesium sulfate; sodium chloride at 40℃; for 120h; Irradiation; Yields of byproduct given. Title compound not separated from byproducts; | |
With Halobacterium halobium; pepton; potassium chloride; sodium citrate; magnesium sulfate; sodium chloride In water at 40℃; for 120h; Irradiation; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
(S)-(-)-2,3-Dihydro-2-methyl-4H-1-benzopyran-4-one
(S)-3-Hydroxybutanoic Acid
Conditions | Yield |
---|---|
With ozone In water; acetic acid for 2h; |
1'(R),6-Dimethyl-4'(S)-isopropyl-4-oxospiro--dioxin>
(S)-3-Hydroxybutanoic Acid
Conditions | Yield |
---|---|
With hydrogen; platinum(IV) oxide In methanol Ambient temperature; |
(S)-3-Hydroxybutanoic Acid
Conditions | Yield |
---|---|
With sodium dihydrogenphosphate; manganese(ll) chloride 1.) 4-oxalocrotonate tautomerase (4-OT), RT, 2 h, 2.) oxalocrotonate decarboxylase, vinylpyruvate hydratase, RT, 1.5 h; Multistep reaction; |
(S)-3-Hydroxybutanoic Acid
Conditions | Yield |
---|---|
With potassium hydroxide In methanol at 50℃; for 0.0833333h; |
(S)-3-(benzyloxy)butanoic acid
(S)-3-Hydroxybutanoic Acid
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal In ethyl acetate for 5h; |
(S)-3-Hydroxybutanoic Acid
Conditions | Yield |
---|---|
With Quinine |
(S)-3-Hydroxybutanoic Acid
Conditions | Yield |
---|---|
With Baecker-yeast |
(S)-3-hydroxybutyric acid methyl ester
A
methanol
B
(S)-3-Hydroxybutanoic Acid
Conditions | Yield |
---|---|
With 2-(di(2-hydroxyethyl)amino)ethanesulfonic acid; lipase from Ophiostoma piliferum In water at 25℃; pH=7.20; Enzyme kinetics; | |
With 2-(di(2-hydroxyethyl)amino)ethanesulfonic acid; lipase from Bacillus thermocatenulanatus In water at 40℃; pH=7.20; Enzyme kinetics; |
Conditions | Yield |
---|---|
With 2-(di(2-hydroxyethyl)amino)ethanesulfonic acid; lipase from Ophiostoma piliferum In water at 25℃; pH=7.20; Enzyme kinetics; | |
With 2-(di(2-hydroxyethyl)amino)ethanesulfonic acid; lipase from Bacillus thermocatenulanatus In water at 40℃; pH=7.20; Enzyme kinetics; |
Conditions | Yield |
---|---|
With sodium hydroxide; dihydrogen peroxide In tetrahydrofuran Title compound not separated from byproducts.; |
(S)-3-hydroxybutyraldehyde
(S)-3-Hydroxybutanoic Acid
Conditions | Yield |
---|---|
With sodium chlorite |
perennisaponin I
A
(S)-3-Hydroxybutanoic Acid
B
polygalacic acid 3-(α-L-rhamnopyranoside)
C
acetic acid
Conditions | Yield |
---|---|
With potassium hydroxide In 1,4-dioxane; water at 40℃; for 12h; | A n/a B 2 mg C n/a |
perennisaponin J
A
(S)-3-Hydroxybutanoic Acid
B
polygalacic acid 3-(α-L-rhamnopyranoside)
C
acetic acid
Conditions | Yield |
---|---|
With potassium hydroxide In 1,4-dioxane; water at 40℃; for 12h; | A n/a B 2 mg C n/a |
perennisaponin K
A
(S)-3-Hydroxybutanoic Acid
B
polygalacic acid 3-(α-L-rhamnopyranoside)
C
acetic acid
Conditions | Yield |
---|---|
With potassium hydroxide In 1,4-dioxane; water at 40℃; for 12h; | A n/a B 2 mg C n/a |
perennisaponin L
A
(S)-3-Hydroxybutanoic Acid
B
polygalacic acid 3-(α-L-rhamnopyranoside)
C
acetic acid
Conditions | Yield |
---|---|
With potassium hydroxide In 1,4-dioxane; water at 40℃; for 12h; | A n/a B 2 mg C n/a |
bortezomib
(S)-3-Hydroxybutanoic Acid
N-[(1S)-1-benzyl-2-({(1R)-3-methyl-1-[(4S)-4-methyl-6-oxo-1,3,2-dioxaborinan-2-yl]butyl}amino)-2-oxoethyl]pyrazine-2-carboxamide
Conditions | Yield |
---|---|
In ethyl acetate at 25 - 60℃; | 96% |
(S)-3-Hydroxybutanoic Acid
Ν,Ν',Ν''-[boroxin-2,4,6-triyltris[[(1R)-3-methylbutane-1,1-diyl]imino(2-oxoethane-2,1-diyl)]]tris(2,5-dichlorobenzamide)
2,5-dichloro-N-[2-({(1R)-3-methyl-1-[(4S)-4-methyl-6-oxo-1,3,2-dioxaborinan-2-yl]butyl}amino)-2-oxoethyl]benzamide
Conditions | Yield |
---|---|
In ethyl acetate at 25 - 60℃; | 95% |
(S)-3-Hydroxybutanoic Acid
benzyl alcohol
3-hydroxybutyric acid benzyl ester
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In chloroform at 0℃; for 6h; | 89% |
(S)-3-Hydroxybutanoic Acid
5-{9-isobutyl-6-[(3S)-3-methylmorpholin-4-yl]-8-piperazin-1-yl-9H-purin-2-yl}pyrimidin-2-amine
(2S)-4-(4-{2-(2-Aminopyrimidin-5-yl)-9-isobutyl-6-[(3S)-3-methylmorpholin-4-yl]-9H-purin-8-yl}piperazin-1-yl)-4-oxobutan-2-ol
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 21h; | 81% |
(S)-3-Hydroxybutanoic Acid
4-methoxy-aniline
(S)-3-hydroxy-N-(4-methoxyphenyl)butanamide
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine; HATU In dichloromethane at 0 - 20℃; Inert atmosphere; | 75% |
Conditions | Yield |
---|---|
With sulfuric acid | 73% |
With sulfuric acid | 73% |
(S)-3-Hydroxybutanoic Acid
benzyl 2-amino-(R)-4,6-O-benzylidene-2-deoxy-β-D-allopyranoside
Conditions | Yield |
---|---|
With 1-hydroxy-pyrrolidine-2,5-dione; triethylamine; dicyclohexyl-carbodiimide In 1,4-dioxane at 20℃; | 72% |
(S)-3-Hydroxybutanoic Acid
3-(5-tert-butyl-1,3,4-oxadiazol-2-yl)-5-(1-methyl-3-(piperidin-4-yl)-1H-1,2,4-triazol-5-yl)pyrazin-2-amine
(3S)-1-[4-[5-[5-amino-6-(5-tert-butyl-1,3,4-oxadiazol-2-yl)pyrazin-2-yl]-1-methyl-1,2,4-triazol-3-yl]-1-piperidyl]-3-hydroxy-butan-1-one
Conditions | Yield |
---|---|
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 2h; Inert atmosphere; | 68% |
(S)-3-Hydroxybutanoic Acid
Conditions | Yield |
---|---|
Stage #1: (S)-3-Hydroxybutanoic Acid; (R)-N-(6-(1-(1-((tert-butyldimethylsilyl)oxy)propan-2-yl)-1H-tetrazol-5-yl)pyridin-2-yl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline-7-carboxamide With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 2h; Stage #2: With hydrogenchloride In water; N,N-dimethyl-formamide at 20℃; for 1h; | 66% |
(S)-3-Hydroxybutanoic Acid
(S)-3-aminocaprolactam hydrochloride
Conditions | Yield |
---|---|
With dmap; 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 24h; | 62% |
(S)-3-Hydroxybutanoic Acid
5-{9-isobutyl-8-[(3R)-3-methylpiperazin-1-yl]-6-morpholin-4-yl-9H-purin-2-yl}pyrimidin-2-amine
(2S)-4-{(2R)-4-[2-(2-Aminopyrimidin-5-yl)-9-isobutyl-6-morpholin-4-yl-9H-purin-8-yl]-2-methylpiperazin-1-yl}-4-oxobutan-2-ol
Conditions | Yield |
---|---|
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 40℃; for 16h; | 61% |
(S)-3-Hydroxybutanoic Acid
5-(9-isobutyl-6-morpholin-4-yl-8-piperazin-1-yl-9H-purin-2-yl)pyrimidin-2-amine
(2S)-4-{4-[2-(2-Aminopyrimidin-5-yl)-9-isobutyl-6-morpholin-4-yl-9H-purin-8-yl]piperazin-1-yl}-4-oxobutan-2-ol
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide for 16h; | 56% |
(S)-3-Hydroxybutanoic Acid
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In tetrahydrofuran at 20℃; for 3h; | 53% |
(S)-3-Hydroxybutanoic Acid
(2S)-4-{4-[2-(2-Aminopyrimidin-5-yl)-6-morpholin-4-yl-9-(2,2,2-trifluoroethyl)-9H-purin-8-yl]piperazin-1-yl}-4-oxobutan-2-ol
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide for 15h; | 50% |
Conditions | Yield |
---|---|
With Dowex 50W In dichloromethane Cyclization; Etherification; Heating; | 48% |
(S)-3-Hydroxybutanoic Acid
5-{9-isobutyl-8-[(3S)-3-methylpiperazin-1-yl]-6-morpholin-4-yl-9H-purin-2-yl}pyrimidin-2-amine
(2S)-4-{(2S)-4-[2-(2-Aminopyrimidin-5-yl)-9-isobutyl-6-morpholin-4-yl-9H-purin-8-yl]-2-methylpiperazin-1-yl}-4-oxobutan-2-ol
Conditions | Yield |
---|---|
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 40℃; for 16h; | 48% |
(S)-3-Hydroxybutanoic Acid
L-cysteine methyl ester hydrochloride
methyl (R)-2-((S)-3-hydroxybutyrylamino)-3-mercaptopropionate
Conditions | Yield |
---|---|
With 4-methyl-morpholine; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In acetonitrile at 0℃; for 3h; | 42% |
3-{[(R)-2,2,5,5-tetramethyl-1,3-dioxan-4-yl]carbonylamino}-1-(2-mercaptoethylamino)-1-propanone
(S)-3-Hydroxybutanoic Acid
dibenzyl phosphochloridate
Conditions | Yield |
---|---|
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 16h; | 40.56% |
(S)-3-Hydroxybutanoic Acid
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In tetrahydrofuran at 20℃; for 16h; | 40% |
(S)-3-Hydroxybutanoic Acid
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; for 2h; | 22% |
(S)-3-Hydroxybutanoic Acid
A
(4S,8S,12S,16S,20S)-4,8,12,16,20-Pentamethyl-1,5,9,13,17-pentaoxa-cycloicosane-2,6,10,14,18-pentaone
B
(4S,8S,12S,16S,20S,24S)-4,8,12,16,20,24-Hexamethyl-1,5,9,13,17,21-hexaoxa-cyclotetracosane-2,6,10,14,18,22-hexaone
C
(4S,8S,12S,16S,20S,24S,28S)-4,8,12,16,20,24,28-Heptamethyl-1,5,9,13,17,21,25-heptaoxa-cyclooctacosane-2,6,10,14,18,22,26-heptaone
Conditions | Yield |
---|---|
With 2,4,6-trichlorobenzoyl chloride; triethylamine In tetrahydrofuran 1.) 0 deg C, 30 min, 2.) 0 deg C to room temperature, 1.5 h; | A 13% B 13% C 7% |
With trichlorobenzoyl chloride; triethylamine In tetrahydrofuran 1.) 0 deg C, 30 min, 2.) 0 deg C to room temperature, 1.5 h; | A 13% B 13% C 7% |
With 2,4,6-trichlorobenzoyl chloride; triethylamine In tetrahydrofuran 1.) 0 deg C, 30 min, 2.) 0 deg C to room temperature; | A 13% B 13% C 7% |
diazomethane
(S)-3-Hydroxybutanoic Acid
(S)-3-hydroxybutyric acid methyl ester
Conditions | Yield |
---|---|
In diethyl ether | 12% |
With diethyl ether | |
In diethyl ether Yield given; | |
In diethyl ether for 0.166667h; Ambient temperature; Yield given; |
Molecular structure of (S)-3-Hydroxybutyric acid (CAS NO.6168-83-8) is:
Product Name: (S)-3-Hydroxybutyric acid
CAS Registry Number: 6168-83-8
IUPAC Name: (3S)-3-hydroxybutanoic acid
Molecular Weight: 104.10452 [g/mol]
Molecular Formula: C4H8O3
XLogP3-AA: -0.5
H-Bond Donor: 2
H-Bond Acceptor: 3
Melting Point: 45-48 °C
Storage temp.: 2-8 °C
Index of Refraction: 1.455
Molar Refractivity: 23.63 cm3
Molar Volume: 87 cm3
Surface Tension: 46.3 dyne/cm
Density: 1.195 g/cm3
Flash Point: 121 °C
Enthalpy of Vaporization: 58.91 kJ/mol
Boiling Point: 269.2 °C at 760 mmHg
Vapour Pressure: 0.000979 mmHg at 25°C
EINECS: 228-209-4
Product Categories: Carboxylic Acids;Chiral Building Blocks;Organic Building Blocks
Safty information about (S)-3-Hydroxybutyric acid (CAS NO.6168-83-8) is:
Hazard Codes: Xi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.
WGK Germany: 3
F: 3-10
(S)-3-Hydroxybutyric acid , its cas register number is 6168-83-8. It also can be called beta-Hydroxybutyrate, L- ; beta-Hydroxybutyrate,l .
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