Isopropyl (2S)-N-(trifluoroacetyl)homoserine
L-homoserine
Conditions | Yield |
---|---|
With ethanol | 95% |
With potassium hydroxide In ethanol for 2h; | 95% |
Conditions | Yield |
---|---|
With water; sodium hydrogencarbonate pH=2 - 5; Reflux; | 92% |
With sodium hydrogencarbonate In water pH=3 - 6; Inert atmosphere; Schlenk technique; Reflux; | 92% |
With sodium hydrogencarbonate In water at 140℃; for 0.5h; | 69% |
Conditions | Yield |
---|---|
With triethylamine In water for 2h; Ambient temperature; | 82% |
2-acetamido-4-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-1-N-(4-L-aspartoyl)-2-deoxy-β-D-glucopyranosylamine
A
L-homoserine
B
N,N'-diacetylchitobiosamine
C
1-acetamido-4-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-2-amino-1,2-dideoxy-D-glucitol
D
2-acetamido-4-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-1-amino-1,2-dideoxy-D-glucitol
Conditions | Yield |
---|---|
With lithium hydroxide; lithium borohydride; trilithium citrate In water; tert-butyl alcohol at 45℃; for 5h; Yield given; | A 80% B 72% C n/a D n/a |
2-acetamido-4-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-1-N-(4-L-aspartoyl)-2-deoxy-β-D-glucopyranosylamine
A
L-homoserine
B
N,N'-diacetylchitobiosamine
C
1-acetamido-4-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-2-amino-1,2-dideoxy-D-glucitol
D
2-acetamido-4-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-1-amino-1,2-dideoxy-D-glucitol
E
β-D-GlcpNAc(1->4)-D-GlcNAc-ol
Conditions | Yield |
---|---|
With lithium hydroxide; lithium borohydride; trilithium citrate In water; tert-butyl alcohol at 45℃; for 5h; Product distribution; | A 80% B 72% C n/a D n/a E 5% |
2-acetamido-4-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-1-N-(4-L-aspartoyl)-2-deoxy-β-D-glucopyranosylamine
A
L-homoserine
B
N,N'-diacetylchitobiosamine
C
2-acetamido-4-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-1-amino-1,2-dideoxy-D-glucitol
D
β-D-GlcpNAc(1->4)-D-GlcNAc-ol
Conditions | Yield |
---|---|
With lithium hydroxide; lithium borohydride; trilithium citrate In water; tert-butyl alcohol at 45℃; for 5h; | A 80% B 72% C n/a D 5% |
Conditions | Yield |
---|---|
With water; methyl iodide at 20℃; for 24h; Inert atmosphere; Reflux; | 74% |
Stage #1: L-methionine With methyl iodide In water for 24h; Inert atmosphere; Stage #2: With potassium hydrogencarbonate for 10h; pH=3 - 6; Reflux; Stage #3: With hydrogenchloride In water pH=5 - 6; | 74% |
Stage #1: L-methionine With methyl iodide In methanol; water for 48h; Stage #2: With sodium hydrogencarbonate In methanol; water for 15h; Reflux; | 62% |
With sodium hydrogencarbonate; methyl iodide In methanol; water for 12h; Reflux; |
(S)-tert-butyl 1-(furan-2-yl)-3-hydroxypropylcarbamate
L-homoserine
Conditions | Yield |
---|---|
Stage #1: (S)-tert-butyl 1-(furan-2-yl)-3-hydroxypropylcarbamate With ozone In methanol at -78℃; for 0.166667h; Stage #2: With dimethylsulfide In methanol at 20℃; for 12h; Stage #3: With hydrogenchloride In 1,4-dioxane at 0 - 20℃; | 62% |
L-methionine
ptaquiloside
A
L-homoserine
B
2(R)-pterosin B
C
(R)-2,5,7-Trimethyl-6-(2-methylsulfanyl-ethyl)-indan-1-one
D
(S)-2-Amino-4-methylsulfanyl-butyric acid 2-((R)-2,4,6-trimethyl-3-oxo-indan-5-yl)-ethyl ester
Conditions | Yield |
---|---|
With sodium hydroxide; Amberlite CG 50 (H form) In water; acetone at 37℃; for 12h; 1.) pH: 9.2; | A 10% B 26% C 12% D 4% |
2-acetamido-4-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-1-N-(4-L-aspartoyl)-2-deoxy-β-D-glucopyranosylamine
A
L-homoserine
B
L-Aspartic acid
C
β-D-GlcpNAc(1->4)-D-GlcNAc-ol
Conditions | Yield |
---|---|
With sodium hydroxide; sodium tetrahydroborate | A 15% B 3% C 20% |
Conditions | Yield |
---|---|
In alkalischen und in verduennten neutralen wss. Loesungen; | |
With water; sodium hydrogencarbonate at 100℃; for 24h; | 8.8 g |
N-chloroacetyl of racemic homoserine lacton
L-homoserine
Conditions | Yield |
---|---|
Enzymatische Herstellung; |
(+)-β-methyl-L-aspartate hydrochloride
L-homoserine
Conditions | Yield |
---|---|
With lithium borohydride In tetrahydrofuran |
L-homoserine
Conditions | Yield |
---|---|
hydrolysis; |
S-methyl-L-methionine hydrobromide
L-homoserine
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In methanol; water for 20h; Heating; Yield given; |
tert-butyl (2S,5S)-2-(tert-butyl)-5-(2-hydroxyethyl)-3-methyl-4-oxo-1-imidazolidinecarboxylate
L-homoserine
Conditions | Yield |
---|---|
With hydrogenchloride; Dowex 50-WX8; acetic acid; trifluoroacetic acid 1.) CH2Cl2, 30 min, 0 deg C; 12 h, room temperature; 2.) 100-105 deg C, toluene, water, 36 h; Yield given. Multistep reaction; |
formaldehyd
(S)-N-(2-benzoylphenyl)-1-benzylpyrrolidine-2-carboxamide
glycine
A
D-Serine
B
L-serin
C
L-homoserine
Conditions | Yield |
---|---|
With nickel nitrate; water; sodium methylate; triethylamine 1.) MeOH, 2 h, 50 deg C; 2.) MeOH, 50 deg C; Yield given. Multistep reaction. Yields of byproduct given; |
Conditions | Yield |
---|---|
With hydrogen; hydrogen In methanol for 20h; Ambient temperature; | A 60 % Spectr. B 40 % Spectr. |
formic acid
L-methionine
A
L-homoserine
B
L-Aspartic acid
C
L-methionine sulfoxide
D
L-glutamic acid
E
L-methionine sulfone
F
L-homocysteic acid
Conditions | Yield |
---|---|
With hydrogen; oxygen In water at 40 - 50℃; Product distribution; Mechanism; A flame from a burner fed with H2-O2 mixtures of different compositions were blown onto the surface of an aq. solution of pH=3; |
L-methionine
A
L-2-aminobutyric acid
B
L-homoserine
C
L-Aspartic acid
D
L-methionine sulfoxide
E
L-methionine sulfone
F
L-homocysteic acid
Conditions | Yield |
---|---|
With hydrogen; oxygen In water at 40 - 50℃; Product distribution; Mechanism; A flame from a burner fed with H2-O2 mixtures of different compositions were blown onto the surface of an aq. solution of pH=3; |
L-methionine
A
L-homoserine
B
L-Aspartic acid
C
L-methionine sulfone
D
L-homocysteic acid
Conditions | Yield |
---|---|
With formic acid; hydrogen; oxygen In water at 40 - 50℃; a flame from a burner fed with H2+O2 was blown to the surface of an aq. solution; H2:O2=50:50; Further byproducts given; |
L-methionine
A
L-homoserine
B
L-Aspartic acid
C
L-methionine sulfoxide
D
L-methionine sulfone
E
(S)-aspartate β-semialdehyde
F
L-homocysteic acid
Conditions | Yield |
---|---|
With hydrogen; oxygen In water Product distribution; various sulfur-containing amino acids under different reaction conditions; |
Conditions | Yield |
---|---|
Equilibrium constant; |
Conditions | Yield |
---|---|
In konzentrierten und in schwach sauren wss. Loesungen; |
L-homoserine
Conditions | Yield |
---|---|
With water; silver(l) oxide at 20℃; |
L-homoserine
Conditions | Yield |
---|---|
With methanol; platinum durch Hydrogenolyse; |
L-S-methylmethionine sulfonium chloride
A
dimethylsulfide
B
L-homoserine
Conditions | Yield |
---|---|
With sodium hydroxide at 100℃; Kinetics; |
L-homoserine
Conditions | Yield |
---|---|
With hydrogenchloride; water at 100℃; for 1h; |
Conditions | Yield |
---|---|
With AHSL acylase Enzymatic reaction; |
Conditions | Yield |
---|---|
With thionyl chloride at 0 - 20℃; for 12.5h; | 100% |
Conditions | Yield |
---|---|
With sodium hydroxide at 2 - 10℃; | 100% |
Conditions | Yield |
---|---|
With hydrogenchloride In water for 0.25h; | 99% |
With hydrogenchloride for 5h; Reflux; | 99% |
With hydrogenchloride a) reflux, 3 h, b) RT, 16 h; | 94% |
Conditions | Yield |
---|---|
With thionyl chloride | 98% |
With thionyl chloride at 0 - 20℃; for 80h; Heating / reflux; | 92% |
L-homoserine
[(p-methylphenyl)sulfonylmethyl]isonitrile
isobutyraldehyde
Conditions | Yield |
---|---|
With 2,2,2-trifluoroethanol at 30 - 40℃; for 94h; | 97% |
Conditions | Yield |
---|---|
Stage #1: L-homoserine; urea In water at 100℃; for 8h; Stage #2: With hydrogenchloride In water at 90℃; for 6h; | 96% |
L-homoserine
di-tert-butyl dicarbonate
L-2-(tert-butyloxycarbonylamino)-4-hydroxybutyric acid
Conditions | Yield |
---|---|
With sodium carbonate In acetone at 19℃; for 8.3h; Temperature; Cooling with ice; | 95% |
With sodium hydroxide In 1,4-dioxane; water at 0 - 25℃; for 24.5h; | 93% |
With sodium hydroxide In water; acetone at 0 - 20℃; for 4h; Reagent/catalyst; | 93% |
L-homoserine
Conditions | Yield |
---|---|
With hydrogen bromide; acetic acid at 80℃; for 6h; Sealed tube; | 95% |
With hydrogen bromide; acetic acid at 80℃; for 5h; |
Conditions | Yield |
---|---|
With sodium carbonate In acetone at 18℃; for 14.6h; Temperature; Cooling with ice; | 94% |
With sodium hydrogencarbonate In water for 3h; | 92% |
With sodium hydrogencarbonate at 20℃; for 24h; | 89% |
Conditions | Yield |
---|---|
With 2,2,2-trifluoroethanol at 30 - 40℃; for 18h; | 93% |
Conditions | Yield |
---|---|
With potassium carbonate In ethanol at 60 - 70℃; diastereoselective reaction; | 93% |
L-homoserine
(S)-cis-3,6-bis-(2-hydroxy-ethyl)-piperazine-2,5-dione
Conditions | Yield |
---|---|
In ethylene glycol at 150℃; for 36h; | 93% |
L-homoserine
[(p-methylphenyl)sulfonylmethyl]isonitrile
pivalaldehyde
Conditions | Yield |
---|---|
With 2,2,2-trifluoroethanol at 30 - 40℃; for 94h; | 92% |
L-homoserine
tert-butyldimethylsilyl chloride
(2S)-amino-4-(tert-butyldimethylsilanyloxy)butanoic acid
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 0 - 20℃; for 16.0833h; | 92% |
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 0 - 20℃; for 16.0833h; | 92% |
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 0 - 20℃; for 16.0833h; | 92% |
Conditions | Yield |
---|---|
With sodium hydroxide In 1,4-dioxane; water for 0.75h; Ambient temperature; | 91% |
L-homoserine
benzyloxycarbonyl-O-benzyl-L-tyrosine 1-succinimidyl ester
C28H30N2O7
Conditions | Yield |
---|---|
With potassium hydrogencarbonate In tetrahydrofuran at 20℃; | 90% |
[ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2
L-homoserine
Conditions | Yield |
---|---|
With sodium hydroxide In methanol at 20℃; for 3.5h; diastereoselective reaction; | 90% |
Conditions | Yield |
---|---|
With sodium hydroxide at 20℃; for 7h; | 89% |
L-homoserine
L-homoserine O-sulfate
Conditions | Yield |
---|---|
With sulfuric acid at 20℃; for 3.5h; | 88% |
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In water; acetone Cooling; | 88% |
L-homoserine
tert-butyl pyridin-2-yl carbonate
L-2-(tert-butyloxycarbonylamino)-4-hydroxybutyric acid
Conditions | Yield |
---|---|
With sodium hydroxide In 1,4-dioxane; water at 0℃; for 24h; | 88% |
Conditions | Yield |
---|---|
With 2,2,2-trifluoroethanol at 30 - 40℃; for 48h; | 87% |
L-homoserine
γ-Cl-Abu
Conditions | Yield |
---|---|
With hydrogenchloride; tetrabutylammomium bromide In water at 80℃; for 9h; Sealed tube; | 87% |
Conditions | Yield |
---|---|
Stage #1: L-homoserine; Allyl chloroformate With sodium carbonate In water; acetonitrile at 20℃; Stage #2: allyl bromide With sodium hydrogencarbonate In N,N-dimethyl-formamide | 86% |
Conditions | Yield |
---|---|
With potassium hydrogencarbonate In diethyl ether; water for 20h; Ambient temperature; | 85% |
Conditions | Yield |
---|---|
With potassium hydrogencarbonate In methanol for 48h; Ambient temperature; | 85% |
L-homoserine
N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
Nα-(Fluoren-9-ylmethoxycarbonyl)-L-homoserine
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In acetonitrile | 85% |
With sodium hydrogencarbonate | |
With sodium carbonate In 1,4-dioxane; water |
L-homoserine
(2S)-2-amino-4-bromobutanoic acid hydrobromide
Conditions | Yield |
---|---|
With hydrogen bromide at 75 - 80℃; for 5h; | 85% |
With hydrogen bromide; acetic acid at 75 - 80℃; for 5h; Autoclave; | 85% |
With hydrogen bromide; acetic acid at 50℃; for 12h; Sealed tube; | 78% |
IUPAC Name: 2-Amino-4-hydroxybutanoic acid
Synonyms of L-Homoserine (CAS NO.672-15-1): Butanoic acid, 2-amino-4-hydroxy-, (S)- ; Homoserine (VAN) ; Butyric acid, 2-amino-4-hydroxy-, L- (8CI)
CAS NO: 672-15-1
Molecular Formula: C4H9NO3
Molecular Weight: 119.12
Molecular Structure:
EINECS: 211-590-6
H bond acceptors: 4
H bond donors: 4
Freely Rotating Bonds: 5
Polar Surface Area: 38.77 Å2
Index of Refraction: 1.51
Molar Refractivity: 27.17 cm3
Molar Volume: 90.7 cm3
Surface Tension: 63.5 dyne/cm
Density: 1.312 g/cm3
Flash Point: 176.8 °C
Enthalpy of Vaporization: 71.22 kJ/mol
Boiling Point: 368.7 °C at 760 mmHg
Vapour Pressure: 6.16E-07 mmHg at 25°C
Melting Point: 203 °C (dec.)(lit.)
Alpha: -8.5 º (c=2, H2O 22 ºC)
Storage temp: Store at RT.
Water Solubility: 1100 g/L (30 °C)
Appearance: white to light yellow crystalline powder
Product Categories of L-Homoserine (CAS NO.672-15-1): Serine [Ser, S];Unusual Amino Acids;Amino Acids;Amino Acids & Derivatives
L-Homoserine (CAS NO.672-15-1) is an intermediate in the biosynthesis of three essential amino acids: methionine, threonine (an isomer of homoserine), and isoleucine.
Safety Information about L-Homoserine (CAS NO.672-15-1):
Safety Statements: 24/25
S24/25: Avoid contact with skin and eyes.
WGK Germany: 3
F: 10
HS Code: 29225000
General Information: As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media: Use water spray, dry chemical, carbon dioxide, or chemical foam.
Handling: Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage: Store in a cool, dry place. Store in a tightly closed container. Keep refrigerated. (Store below 4°C/39°F.)
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