N-(9-fluorenylmethoxycarbonyl)-D-leucine
(R)-leucine
Conditions | Yield |
---|---|
With piperidine In N,N-dimethyl-formamide at 20℃; | 100% |
(R)-N-benzylleucine
(R)-leucine
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal In acetic acid for 24h; | 98% |
(R)-2-azido-4-methylpentanoic acid
(R)-leucine
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal In water; acetic acid under 760 Torr; for 4h; | 92% |
D-α-Hydrazino-isocapronsaeure
(R)-leucine
Conditions | Yield |
---|---|
With hydrogen; platinum(IV) oxide | 91% |
(R)-2-Amino-4-methyl-pentanoic acid ((1S,2S)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide
A
(R)-leucine
B
pseudoephedrine
Conditions | Yield |
---|---|
With water for 10h; Heating; | A 86% B n/a |
(R)-2-Amino-4-methyl-pentanoic acid ((1S,2S)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide
(R)-leucine
Conditions | Yield |
---|---|
In water for 10h; Heating; other reagent; | 86% |
Conditions | Yield |
---|---|
With D-glucose; Bacillus subtilis glucose dehydrogenase; Symbiobacterium thermophilum meso-Diaminopimelate dehydrogenase W121L/H227I mutant; NADP; ammonium chloride In aq. buffer at 37℃; for 24h; pH=8.5; Kinetics; Reagent/catalyst; Enzymatic reaction; | 68% |
With D-Alanine; meso-diaminopimelate dehydrogenase; pyridoxal 5'-phosphate; alcohol dehydrogenases from Bacillus stearothermophilus; alcohol dehydrogenases from Thermoanaerobacter brockii; NADH In isopropyl alcohol at 35℃; for 12h; pH=8; Reagent/catalyst; Enzymatic reaction; enantioselective reaction; | 53.2% |
With meso-2,6-D-diaminopimelic acid dehydrogenase mutant BC621; ammonium chloride; NADPH In various solvent(s) for 24h; | |
With D-amino acid transaminase; D-Alanine; R-selective ω-transaminase from Arthrobacter sp; (3-hydroxy-5-hydroxymethyl)-2-methylisonicotinic acid 5-phosphate; isopropylamine In aq. phosphate buffer for 7h; pH=7; | n/a |
With D-Glucose; Bacillus megaterium glucose dehydrogenase; ammonia; Symbiobacterium thermophilum mesodiaminopimelate dehydrogenase Enzymatic reaction; | n/a |
Conditions | Yield |
---|---|
With zinc(II) perchlorate; (S)-15-amino-methyl-14-hydroxy-5,5-dimethyl-2,8-dithia<9>(2,5)pyridinophane In methanol for 24h; Ambient temperature; | 66% |
Conditions | Yield |
---|---|
With yeast; Sucrose | |
beim Durchgang durch den Organismus des Kaninchens; | |
With penicillium glaucum |
Conditions | Yield |
---|---|
With (-)-(R,R)-dibenzoyltartaric acid |
Conditions | Yield |
---|---|
With ethanol; brucine man filtriert das sich ausscheid.Brucinsalz des Formyl-d-leucins ab,zerlegt es durch Natronlauge u.verseift das erhalt.Formyl-d-leucin durch Kochen mit 10prozentig.Salzsaeure o.durch Schuetteln mit 30prozentig.Bromwasserstoffsaeure b.37grad; |
N-formyl-D-leucine
(R)-leucine
Conditions | Yield |
---|---|
Hydrolysis; |
N-chloroacetyl-D-leucine
(R)-leucine
Conditions | Yield |
---|---|
With hydrogenchloride |
Z-D-Leu-OH
(R)-leucine
Conditions | Yield |
---|---|
With hydrogenchloride; palladium Hydrogenation; |
N-acetyl-D-leucine
(R)-leucine
Conditions | Yield |
---|---|
In water at 37℃; for 0.166667h; Rate constant; D-aminocyclase from Alcaligenes denitrificans DA181, pH 7.8, bovine serum albumin; | |
With D-aminoacylase from Alcaligenes xylosoxydans Enzyme kinetics; Further Variations:; Reagents; Deacetylation; |
isobutyl triflate
trans-(2S,5S)-N--2,5-bis(methoxymethoxymethyl)pyrrolidine
A
(R)-leucine
B
L-leucine
Conditions | Yield |
---|---|
Yield given. Multistep reaction. Yields of byproduct given; |
glycyl-L-leucylglycylglycine
A
(R)-leucine
B
[(S)-2-(2-Amino-acetylamino)-4-methyl-pentanoylamino]-acetic acid
C
glycyl-D-leucylglycine
D
glycyl-D-leucylglycylglycine
E
cyclo(glycyl-L-leucyl)
F
cyclo-(glycyl-D-leucyl)
Conditions | Yield |
---|---|
In various solvent(s) at 148.5℃; Product distribution; Rate constant; rate of racemization was investigated during decomposition; |
Conditions | Yield |
---|---|
With (R)-<methyl>pyridine; copper(II) ion In various solvent(s) at 25℃; Rate constant; enantioselectivity of cleavage; other chiral ligands; |
(2R,2'R)-N-(2'-amino-4'-methylpentanoyl)bornane-10,2-sultam
(R)-leucine
Conditions | Yield |
---|---|
With lithium hydroxide; ion exchange 1.) THF; Yield given. Multistep reaction; | |
With lithium hydroxide; Amberlite IR-120 1) THF, room temperature, 2) H2O, room temperature, 15 h; Yield given. Multistep reaction; |
theonellamine B
A
N-methylalanine
B
L-valine
C
L-threonine
D
N-methyl-L-valine
E
(R)-leucine
F
3-amino propanoic acid
Conditions | Yield |
---|---|
With hydrogenchloride at 110℃; for 4h; |
theonellamine B
A
L-valine
B
N-methyl-L-valine
C
(R)-leucine
D
3-amino propanoic acid
Conditions | Yield |
---|---|
With hydrogenchloride at 110℃; for 40h; Further byproducts given; |
Conditions | Yield |
---|---|
With hydrogen; Pd-BaSO4 In ethanol under 760 Torr; Ambient temperature; Yield given. Yields of byproduct given; |
Conditions | Yield |
---|---|
With triphenyl phosphite; oxygen In dichloromethane Product distribution; Ambient temperature; configuration; |
L-leucine (phenylmethyl)ester
A
(R)-leucine
B
L-leucine
C
L-Leucine benzyl ester
D
D-leucine benzyl ester
Conditions | Yield |
---|---|
With sodium bicarbonate buffer; subtilisin 8350 at 35℃; for 1h; Product distribution; var. DL-amino acid esters; |
9-fluorenylmethyloxycarbonyl-L-leucine anhydride
A
(R)-leucine
B
L-leucine
Conditions | Yield |
---|---|
With dmap; p-hydroxymethylphenoxyacetyl-polydimethylacrylamide resin; trifluoroacetic acid Product distribution; racemisation in dependence on sequence of addition of reagents; 1) dimethylacetamide, 3 h; |
N-carbamyl-D-leucine
(R)-leucine
Conditions | Yield |
---|---|
With potassium phosphate buffer; Pseudomonas sp. AJ-11220 In various solvent(s) at 30℃; for 2h; | |
With hydrogenchloride; sodium nitrite at 0℃; | |
With potassium phosphate buffer; Pseudomonas sp. AJ-11220 In various solvent(s) at 30℃; for 2h; pH 7.5; enzymatic reaction; |
5-isobutyl-imidazolidine-2,4-dione
(R)-leucine
Conditions | Yield |
---|---|
at 37℃; Pseudomonas Sp.; |
Conditions | Yield |
---|---|
With hydrogenchloride 1.) THF, from -78 to -40 degC; 2.) reflux; Yield given. Multistep reaction; |
methanol
(R)-leucine
(R)-leucine methyl ester hydrochloride
Conditions | Yield |
---|---|
With sulfuryl dichloride at 0 - 20℃; for 16h; Inert atmosphere; | 100% |
With thionyl chloride at 20℃; | 99% |
With thionyl chloride for 12h; Ambient temperature; | 94% |
Conditions | Yield |
---|---|
With sodium hydroxide In water at 0 - 20℃; | 100% |
With sodium hydroxide In water at 20℃; for 2h; | 90% |
With sodium hydrogencarbonate | 87% |
Stage #1: (R)-leucine With sodium hydroxide In water at 0℃; Cooling with ice; Stage #2: benzyl chloroformate In 1,4-dioxane; water at 20℃; | |
With sodium hydroxide In 1,4-dioxane at 0 - 20℃; |
Conditions | Yield |
---|---|
With thionyl chloride for 4h; Reflux; | 100% |
With hydrogenchloride Heating; | 87% |
phthalic anhydride
(R)-leucine
(R)-2-(1,3-dioxoisoindolin-2-yl)-4-methylpentanoic acid
Conditions | Yield |
---|---|
for 0.0611111h; microwave irradiation; | 98% |
at 150℃; |
(R)-leucine
N-1-naphthalenesulfonyl-D-leucine
Conditions | Yield |
---|---|
With hydrogenchloride In 1,4-dioxane | 98% |
(R)-leucine
1-Naphthalenesulfonyl chloride
N-1-naphthalenesulfonyl-D-leucine
Conditions | Yield |
---|---|
With sodium hydroxide In 1,4-dioxane at 0 - 20℃; for 4h; pH=9 - 10; | 98% |
Conditions | Yield |
---|---|
With sodium hydroxide In 1,4-dioxane at 0 - 20℃; Inert atmosphere; | 97% |
Stage #1: (R)-leucine With sodium hydroxide In tetrahydrofuran; water for 0.25h; Inert atmosphere; Cooling with ice; Stage #2: di-tert-butyl dicarbonate In tetrahydrofuran; water at 20℃; for 24h; pH=Ca. 10.5; Inert atmosphere; Cooling with ice; | 97.2% |
Stage #1: (R)-leucine With potassium carbonate In acetone at 20℃; for 0.0833333h; Stage #2: di-tert-butyl dicarbonate In acetone | 95% |
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide Microwave irradiation; | 97% |
N-succinimidyl 3,5-dichlorobenzoate
(R)-leucine
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In tetrahydrofuran; water at 20℃; for 18h; | 97% |
(R)-leucine
4-bromobenzenesulfonyl chloride
N-p-bromo-benzenesulfonyl-D-leucine
Conditions | Yield |
---|---|
With hydrogenchloride In 1,4-dioxane | 96.4% |
(R)-leucine
4-bromobenzenesulfonyl chloride
N-p-bromobenzenesulfonyl-D-leucine
Conditions | Yield |
---|---|
With sodium hydroxide In 1,4-dioxane at 0 - 20℃; for 4h; pH=9 - 10; | 96.4% |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In benzene for 16h; Heating; | 95% |
Conditions | Yield |
---|---|
With potassium phosphate In tetrahydrofuran for 24h; Inert atmosphere; | 94% |
With sodium hydroxide for 2.5h; Ambient temperature; |
Conditions | Yield |
---|---|
With sodium hydroxide In 1,4-dioxane at 0 - 20℃; for 4h; pH=9 - 10; | 94% |
With sodium carbonate In water |
(R)-leucine
di(μ-chloro)bis[1-(phenylazo)phenyl-C(2)N]dipalladium(II)
Conditions | Yield |
---|---|
With NaOMe In methanol N2-atmosphere; dropwise addn. of 1 equiv. NaOMe to aminoacid, gentle heating to dissoln., addn. of stoich. amt. Pd-complex, stirring for 15 h; solvent removal (vac.), dissoln. in CH2Cl2, centrifugation, solvent removal (vac.); elem. anal.; | 94% |
Conditions | Yield |
---|---|
With hydrogenchloride In 1,4-dioxane | 94% |
(R)-leucine
(R)-2-hydroxy-4-methylpentanoic acid
Conditions | Yield |
---|---|
With sulfuric acid; sodium nitrite In water at 5 - 20℃; | 93.8% |
With sulfuric acid; sodium nitrite at 0℃; | 79% |
With sulfuric acid; water; sodium nitrite | 76% |
Conditions | Yield |
---|---|
With thionyl chloride for 6h; Ambient temperature; | 91% |
With chlorosulfonic acid at 20℃; for 2h; | 80% |
With hydrogenchloride |
(R)-leucine
N-t-butoxycarbonyl-(R)-proline N-hydroxysuccuinimide ester
N-(tert-butoxycarbonyl)-(R)-prolyl-(R)-leucine
Conditions | Yield |
---|---|
With sodium hydroxide; potassium hydrogencarbonate In 1,4-dioxane 1.) 0 deg C, overnight; 2.) r.t., 24 h; | 90% |
Conditions | Yield |
---|---|
Stage #1: (R)-leucine; acetic anhydride With sodium hydroxide In water at 5 - 15℃; for 4 - 5h; Stage #2: With hydrogenchloride In water at 5 - 15℃; for 2.5h; | 89% |
Stage #1: (R)-leucine; acetic anhydride With sodium hydroxide In water at 5 - 15℃; for 2h; pH=8-9; Inert atmosphere; Large scale; Stage #2: With hydrogenchloride In water at 5 - 15℃; for 2.5h; Inert atmosphere; Large scale; | 89% |
With sodium hydroxide In water at 20℃; pH=14; | |
In tetrahydrofuran; water |
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In water; acetonitrile at 20℃; for 0.5h; pH=8.5; | 88.7% |
(R)-leucine
Conditions | Yield |
---|---|
Stage #1: (R)-leucine With dicyclohexyl-carbodiimide In dichloromethane for 0.333333h; Stage #2: N-((1S,2R,4aS,5R,8aS)-2-hydroxy-1,4a-dimethyl-6-methylene-5-((E)-2-(2-oxo-2,5-dihydrofuran-3-yl)ethenyl)decahydronaphthalen-1-yl)formamide With dmap In dichloromethane at 20℃; for 2h; | 88% |
(R)-leucine
(1R,2S,5R)-menthyl chloroformate
N-[(-)-menthoxylcarbonyl]-D-leucine
Conditions | Yield |
---|---|
With sodium hydroxide In water at 0℃; for 0.5h; Schlenk technique; Inert atmosphere; | 87% |
(R)-leucine
(R)-2-bromo-4-methylpentanoic acid
Conditions | Yield |
---|---|
With hydrogen bromide; sodium nitrite In water at 0℃; for 2.5h; | 86% |
With hydrogen bromide; sodium nitrite In water at 0℃; for 2.5h; Inert atmosphere; | 85% |
With potassium bromide; sodium nitrite In water | 83% |
Reported in EPA TSCA Inventory.
The D-Leucine, with the cas register number 328-38-1, has its IUPAC name of 2-amino-4-methylpentanoic acid. This is a kind of flaky crystalline powder, and soluble in water, acetic acid, slightly soluble in ethanol, and insoluble in diethyl [ethyl] ether. The product categories are including leucine [leu, l]; amino acids and derivatives; alpha-amino acids; amino acids; biochemistry; amino acids. It should be kept in the storage temp. -15°C. Besides, it is usually applied in biochemical study.
The physical properties of this chemical could be summarized as: (1)ACD/LogP: 0.73; (2)# of Rule of 5 Violations: 0; (3)ACD/BCF (pH 5.5): 1; (4)ACD/BCF (pH 7.4): 1; (5)ACD/KOC (pH 5.5): 1; (6)ACD/KOC (pH 7.4): 1; (7)#H bond acceptors: 3; (8)#H bond donors: 3; (9)#Freely Rotating Bonds: 4; (10)Polar Surface Area: 29.54; (11)Index of Refraction: 1.462; (12)Molar Refractivity: 34.86 cm3; (13)Molar Volume: 126.6 cm3; (14)Polarizability: 13.82 ×10-24 cm3; (15)Surface Tension: 39 dyne/cm; (16)Density: 1.035 g/cm3; (17)Flash Point: 90.3 °C; (18)Enthalpy of Vaporization: 50.93 kJ/mol; (19)Boiling Point: 225.8 °C at 760 mmHg; (20)Vapour Pressure: 0.0309 mmHg at 25°C.
As to its production method, please follow the below ways. Firstly, prepare the raw material of acetyl-DL-leucine, and go through the acylase treatment to remove L-leucine, and then hydrolyze in hydrochloric [chlorhydric] acid to get the crude products; Lastly, have the crystalline purification to get the puregrade.
When you are using this chemical, you should be very cautious. Being a kind of irritant chemical, it is irritating to eyes, respiratory system and skin, and may cause inflammation to the skin or other mucous membranes. So while dealing with this chemical, you should take the following instructions. Wear suitable protective clothing. Do not breathe dust and avoid contacting with skin and eyes. And if in case of contacting with eyes, rinse immediately with plenty of water and seek medical advice. You could also refer to WGK Germany 3 to obtain more safety information.
Additionally, you could convert the following datas information into the molecular structure:
(1)Canonical SMILES: CC(C)CC(C(=O)O)N
(2)InChI: InChI=1S/C6H13NO2/c1-4(2)3-5(7)6(8)9/h4-5H,3,7H2,1-2H3,(H,8,9)
(3)InChIKey: ROHFNLRQFUQHCH-UHFFFAOYSA-N
Below are the toxcity information of this chemical:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
rat | LD50 | intraperitoneal | 6429mg/kg (6429mg/kg) | BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) LUNGS, THORAX, OR RESPIRATION: DYSPNEA | Archives of Biochemistry and Biophysics. Vol. 64, Pg. 319, 1956.
|
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