(R)-3-Hydroxy-2-((R)-2-methoxy-1-phenyl-ethylamino)-propionic acid tert-butyl ester
D-Serine
Conditions | Yield |
---|---|
With hydrogen; palladium dihydroxide In ethanol; water | 100% |
(2R)-1-tritylaziridine-2-carboxylic acid methyl ester
D-Serine
Conditions | Yield |
---|---|
With perchloric acid for 30h; Heating; | 97% |
Conditions | Yield |
---|---|
With pyridoxal 5'-phosphate; D-threonine aldolase (DTA) P3005; magnesium chloride In water at 30℃; for 24h; pH=7.3; pH-value; Concentration; Temperature; Large scale; Enzymatic reaction; | 97% |
With pyridoxal 5'-phosphate; D-threonine aldolase from Arthrobacter sp ATCC at 30℃; for 16h; pH=7; Reagent/catalyst; Temperature; pH-value; Enzymatic reaction; enantioselective reaction; | 84% |
Stage #1: glycine With (S)-N-(2-benzoylphenyl)-1-(2-chlorobenzyl)pyrrolidine-2-carboxamide; sodium methylate; nickel(II) nitrate In methanol at 50℃; Stage #2: formaldehyd With sodium methylate In methanol at 20℃; optical yield given as %ee; enantioselective reaction; Further stages; |
Conditions | Yield |
---|---|
With isopropylamine In aq. buffer for 20h; pH=7.0; Enzymatic reaction; | 95% |
With (R)-selective ω-transaminase from arthrobacter sp.; isopropylamine In aq. phosphate buffer at 37℃; for 2h; pH=7; Reagent/catalyst; Enzymatic reaction; | n/a |
D-Serine
Conditions | Yield |
---|---|
With ammonia; lithium In tetrahydrofuran; tert-butyl alcohol at -78℃; for 0.5h; | 94% |
(R)-3-Benzyloxy-2-((R)-2-oxo-4-phenyl-oxazolidin-3-yl)-propionic acid
D-Serine
Conditions | Yield |
---|---|
With ammonia; lithium In tetrahydrofuran; tert-butyl alcohol at -78℃; for 0.5h; Birch reduction; | 94% |
(R)-2-acetamido-3-hydroxypropanoic acid
D-Serine
Conditions | Yield |
---|---|
With hydrogenchloride In methanol | 85% |
With Agrobacterium tumefaciens C58 recombinant Atu3266 protein; water at 30℃; for 15h; pH=7.6; Enzymatic reaction; |
D-Serine
Conditions | Yield |
---|---|
Stage #1: C15H15N3*C10H9Cl2NO4 With hydrogenchloride In acetonitrile at 20℃; for 1h; Stage #2: With triethylamine In ethanol; dichloromethane at 20℃; for 1h; | 85% |
(1'S,5R)-1-(benzyloxycarbonyl)-3-(1'-phenyleth-1'-yl)-5-(hydroxymethyl)imidazolidin-4-one
D-Serine
Conditions | Yield |
---|---|
With hydrogenchloride In methanol for 24h; Heating; | 65% |
D-Serine
Conditions | Yield |
---|---|
With perchloric acid at 80℃; for 0.5h; | 65% |
Conditions | Yield |
---|---|
Vergaerung durch Hefe in Gegenwart von Zucker; | |
Stage #1: serin at 37℃; for 42h; pH=7.3 - 7.4; Microbiological reaction; aq. phosphate buffer; Inert atmosphere; Stage #2: pH=7.3 - 7.4; aq. phosphate buffer; Stage #3: With ammonia In water enantioselective reaction; | 3.47 g |
Stage #1: serin With tetraphenyl phosphonium chloride In 1,2-dichloro-ethane for 2h; Resolution of racemate; Flow reactor; Stage #2: With sodium hydroxide In water Stage #3: With hydrogenchloride; water for 1h; Reagent/catalyst; enantioselective reaction; | n/a |
With N-ethyl-N,N-diisopropylamine; sodium hydroxide In water; 1,2-dichloro-ethane for 1h; Enzymatic reaction; enantioselective reaction; |
N-chloroacetyl-D-serine
D-Serine
Conditions | Yield |
---|---|
With hydrogenchloride |
D-serine benzyl ester
D-Serine
Conditions | Yield |
---|---|
With hydrogenchloride | |
With Streptomyces spp. 82F2 D-aminopeptidase In dimethyl sulfoxide at 20℃; for 0.0833333h; pH=6.5; aq. buffer; Enzymatic reaction; |
(R)-2-(isoindolin-2-yl)-3-methoxypropanoic acid
D-Serine
Conditions | Yield |
---|---|
With hydrogen iodide; acetic acid |
Conditions | Yield |
---|---|
In water at 140℃; Rate constant; pH 8.0; | |
In water at 140℃; Mechanism; pH 8.0; other neutral, hydroxy, thioether, and acidic amino acids; | |
With Geobacillus stearothermophilus alanine racemase with an asparagine mutation at Tyr354 pH=7.5; aq. phosphate buffer; Enzymatic reaction; | |
With recombinant rat serine racemase; pyridoxal 5'-phosphate; ATP; magnesium chloride In water at 37℃; pH=9; Kinetics; Concentration; Reagent/catalyst; aq. buffer; Enzymatic reaction; |
D-Serine
Conditions | Yield |
---|---|
hydrolysis; |
(2R)-3-benzyloxy-2-aminopropanoic acid methyl ester
D-Serine
Conditions | Yield |
---|---|
With hydrogenchloride Heating; | |
With hydrogenchloride; methyloxirane 1.) H2O, reflux, 3 h, 2.) EtOH, reflux, 15 min; Yield given. Multistep reaction; |
(2R)-2-amino-3-hydroxypropanoic acid hydrochloride
D-Serine
Conditions | Yield |
---|---|
With methyloxirane In ethanol for 0.25h; Heating; Yield given; |
2,2',ΔAla4,D-Ser4'>-GS
A
L-alanin
B
L-valine
C
D-Serine
D
L-leucine
E
L-ornithine
F
L-proline
Conditions | Yield |
---|---|
With hydrogen Product distribution; |
C58H100N12O16
A
L-alanin
B
D-Serine
C
L-leucine
D
L-ornithine
E
2-oxo-propionic acid
F
L-proline
Conditions | Yield |
---|---|
With hydrogen Product distribution; |
luzopeptin C
A
sarcosine
B
D-Serine
C
L-β-hydroxy-N-methylvaline
D
glycine
Conditions | Yield |
---|---|
With hydrogenchloride at 100℃; for 18h; Further byproducts given; |
luzopeptin C
A
sarcosine
B
D-Serine
C
3-hydroxy-6-methoxyquinoline-2-carboxylic acid
D
glycine
Conditions | Yield |
---|---|
With hydrogenchloride at 100℃; for 18h; Further byproducts given; |
formaldehyd
(S)-N-(2-benzoylphenyl)-1-benzylpyrrolidine-2-carboxamide
glycine
A
D-Serine
B
L-serin
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; |
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 styrene-divinylbenzene copolymer containing different quantity of (S)-2N-(prolyl)aminobenzophenone groups on it; triethylamine Product distribution; further tertiary amine; |
Conditions | Yield |
---|---|
With water In various solvent(s) Rate constant; Irradiation; radiolysis, var. pH; |
N-carbamyl-D-serine
D-Serine
Conditions | Yield |
---|---|
With hydrogenchloride; sodium nitrite at 0℃; |
A
D-Serine
B
L-threonine
C
(R)-leucine
D
L-isoleucine
E
(2R)-aspartic acid
F
L-Aspartic acid
Conditions | Yield |
---|---|
With hydrogenchloride at 120℃; for 20h; Product distribution; |
A
D-Serine
Conditions | Yield |
---|---|
With disodium hydrogenphosphate; sodium dihydrogenphosphate In water at 25℃; pH=7.20; Equilibrium constant; Further Variations:; Temperatures; decomplexation; |
Conditions | Yield |
---|---|
With hydrogenchloride for 18h; Heating; | 100% |
Stage #1: methanol With acetyl chloride at 0℃; for 0.333333h; Stage #2: D-Serine for 2h; Reflux; | 99% |
With hydrogenchloride at 20℃; for 16h; | 97% |
Conditions | Yield |
---|---|
With acetyl chloride for 2.5h; Heating; | 100% |
Stage #1: methanol; D-Serine With acetyl chloride at 0℃; Stage #2: In methanol for 3h; Heating; | 100% |
With hydrogenchloride In water at 55℃; | 100% |
D-Serine
di-tert-butyl dicarbonate
(R)-N-tert-butoxycarbonyl serine
Conditions | Yield |
---|---|
With sodium hydroxide In 1,4-dioxane; water at 0 - 25℃; for 2h; | 100% |
With sodium hydrogencarbonate; sodium carbonate In 1,4-dioxane at 0 - 20℃; | 100% |
With sodium hydrogencarbonate; sodium carbonate In 1,4-dioxane; water at 0 - 20℃; for 24.5h; | 100% |
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In methanol; water at 20℃; for 0.5h; Green chemistry; | 100% |
With acetic acid for 24h; Ambient temperature; | |
In acetic acid at 20℃; for 24h; |
Conditions | Yield |
---|---|
In methanol | A n/a B 99% |
D-Serine
(R)-N-tert-butoxycarbonyl serine
Conditions | Yield |
---|---|
With di-tert-butyl dicarbonate; sodium hydroxide In 1,4-dioxane; water at 0 - 20℃; for 7h; | 99% |
methanol
D-Serine
di-tert-butyl dicarbonate
2-(tert-butoxycarbonylamino)-3-hydroxypropionic acid methyl ester
Conditions | Yield |
---|---|
Stage #1: methanol; D-Serine With acetyl chloride for 2h; Heating; Stage #2: di-tert-butyl dicarbonate With triethylamine In dichloromethane at 0 - 20℃; for 3h; Further stages.; | 98% |
Stage #1: methanol; D-Serine With thionyl chloride at 0 - 20℃; for 6h; Stage #2: di-tert-butyl dicarbonate With sodium hydrogencarbonate In 1,4-dioxane; water at 20℃; for 12h; |
D-Serine
(2R)-2-amino-3-hydroxypropanoic acid hydrochloride
Conditions | Yield |
---|---|
With thionyl chloride In methanol at 0 - 20℃; | 98% |
Conditions | Yield |
---|---|
With sodium methylate In methanol at 20℃; for 12h; Darkness; | 98% |
methanol
D-Serine
acetyl chloride
R-(-)-serine methyl ester hydrochloride
Conditions | Yield |
---|---|
Stage #1: methanol; acetyl chloride for 0.0833333h; Cooling with ice; Stage #2: D-Serine for 2h; Reflux; | 97% |
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In tetrahydrofuran; water at 20℃; for 12h; | 96% |
Stage #1: D-Serine With sodium hydrogencarbonate In water at 0 - 5℃; Stage #2: benzyl chloroformate In water; toluene at 0 - 20℃; | 95% |
With sodium hydrogencarbonate at 20℃; for 4h; | 91% |
D-Serine
2-(1-hydroxy-3-methylbutylidene)-5,5-dimethylcyclohexane-1,3-dione
N-(ivDde)-D-serine
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In methanol Heating / reflux; | 96% |
Conditions | Yield |
---|---|
With sodium carbonate at 20℃; for 24h; Substitution; | 95% |
Conditions | Yield |
---|---|
In tetrachloromethane for 9h; Heating; | 95% |
D-Serine
N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
(R)-N-(fluoren-9-ylmethoxycarbonyl)serine
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In 1,4-dioxane; water | 95% |
Conditions | Yield |
---|---|
In methanol for 10h; Heating; | 92% |
Conditions | Yield |
---|---|
With triethylamine; 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 3h; | 91.2% |
Conditions | Yield |
---|---|
With potassium carbonate In ethanol; water at 100℃; for 10h; | 91% |
Conditions | Yield |
---|---|
In methanol for 15.5h; Reflux; | 91% |
D-Serine
D-2-amino-3-chloropropionic acid chloride hydrochloride
Conditions | Yield |
---|---|
Stage #1: D-Serine With hydrogenchloride In chloroform for 0.166667h; Stage #2: With thionyl chloride In chloroform at 0℃; Reflux; | 90% |
With phosphorus pentachloride; acetyl chloride at 20℃; for 4h; | 89% |
Conditions | Yield |
---|---|
With sodium carbonate In water; acetonitrile at 5 - 20℃; for 12.5h; | 89% |
With sodium carbonate In water; acetonitrile at 20℃; for 30h; | |
With sodium carbonate In water; acetonitrile at 20℃; for 8h; Cooling with ice; | |
With sodium carbonate In 1,4-dioxane; water Inert atmosphere; | |
With sodium carbonate In water; acetonitrile at 20℃; for 30h; |
D-Serine
benzyl N-[(1S)-2-(1H-1,2,3-benzotriazol-1-yl)-1-methyl-2-oxoethyl]carbamate
(2R)-2-((2S)-2-(((benzyloxy)carbonyl)amino)propanamido)-3-hydroxypropanoic acid
Conditions | Yield |
---|---|
With triethylamine In water; acetonitrile at 20℃; for 2h; | 89% |
D-Serine
(R)-N-tert-butoxycarbonyl serine
Conditions | Yield |
---|---|
With triethylamine In water; acetone at 25℃; for 11h; Temperature; | 89% |
Conditions | Yield |
---|---|
Stage #1: D-Serine; benzaldehyde With sodium hydroxide In water at 20℃; for 1h; Stage #2: With sodium tetrahydroborate In water at 5 - 20℃; for 17.5h; Stage #3: With hydrogenchloride In water pH=5; | 88% |
Stage #1: D-Serine; benzaldehyde With sodium hydroxide In water at 20℃; for 1h; Stage #2: With sodium tetrahydroborate In water at 5 - 20℃; for 17.5h; | 88% |
Stage #1: D-Serine; benzaldehyde With sodium hydroxide In water at 20℃; for 1h; Stage #2: With sodium tetrahydroborate In water at 5 - 20℃; | 88% |
Stage #1: D-Serine; benzaldehyde With sodium hydroxide In water at 20℃; for 0.5h; Stage #2: With sodium tetrahydroborate In water at 6 - 20℃; for 4.41h; ice-salt bath; Stage #3: With hydrogenchloride; water pH=~ 6.5; | 46% |
With sodium hydroxide; sodium tetrahydroborate 1) 30 min; 2) 6-10 deg C; Yield given. Multistep reaction; |
The D-Serine, with the cas register number 312-84-5, has other names as d-(+)-serine; d-serine; d-2-amino-3-hydroxypropionic acid; d-2-amino-3-hydroxypropanoic acid; d-beta-hydroxyalanine; h-d-ser-oh; 2-amino-3-hydroxypropanoic acid; (r)-2-amino-3-hydroxypropionic acid.
The physical characteristics of this chemical could be summarized as: (1)ACD/LogP: -1.58; (2)ACD/LogD (pH 5.5): -4.08; (3)ACD/LogD (pH 7.4): -4.08; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 1; (7)ACD/KOC (pH 7.4): 1; (8)#H bond acceptors: 4; (9)#H bond donors: 4; (10)#Freely Rotating Bonds: 4; (11)Polar Surface Area: 38.77; (12)Index of Refraction: 1.519; (13)Molar Refractivity: 22.54 cm3; (14)Molar Volume: 74.2 cm3; (15)Polarizability: 8.93 ×10-24 cm3; (16)Surface Tension: 72.2 dyne/cm; (17)Density: 1.415 g/cm3; (18)Flash Point: 192.6 °C; (19)Enthalpy of Vaporization: 74.56 kJ/mol; (20)Boiling Point: 394.8 °C at 760 mmHg; (21)Vapour Pressure: 7.17E-08 mmHg at 25°C.
This is a kind of white powder, and its water solubility is 346 g/L (20 ºC). Being among the irritant chemicals, it is irritating to eyes, respiratory system and skin, and it may cause inflammation to the skin or other mucous membranes. So while dealing with this chemical, you should be very cautious and had better take the following instructions. The first important thing is to wear suitable protective clothing. And avoid contact with skin and eyes, if in case of contacting with eyes, rinse immediately with plenty of water and seek medical advice. And you could also convert to the WGK Germany 3 to get more safety information.
When comes to its usage, it is widely applied in many ways. It could be used in curing inflammatory disease, such as temple arteritis and multiple rheumatic disease; Then it could also be used in biochemical study, preparation in TCM Tissue Culture Medium, Amino Acids-like nutriceutical in medicine; Besides, it could also be as the pharmaceutic intermediate and chemical reagents.
As to its product categories, there are various, including amino acid derivatives; serine [ser, s]; amino acids and derivatives; alpha-amino acids; amino acids; biochemistry; amino acids; glutamate receptor; glutamate; while its raw materials are chloroacetyl chloride, 2-n-butoxyethyl methacrylate, dl-serine, and aminoacylase.
The simple way to produce this chemical is below: DL-serine reacts with chloroacetic chloride in alkaling conndition and then go through a list of process of decompressing, drying by distillation, extracting by ethyl acetate, and then have the activated carbontreatment and splitting of acylaseI, finally, you could get this chemical.
In addition, you could refer to the following information to obtain the molecular structure:
SMILES:O=C(O)[C@H](N)CO
InChI:InChI=1/C3H7NO3/c4-2(1-5)3(6)7/h2,5H,1,4H2,(H,6,7)/t2-/m1/s1
InChIKey:MTCFGRXMJLQNBG-UWTATZPHBH
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