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CAS No.: | 4515-23-5 |
---|---|
Name: | N-CARBOBENZYLOXY-L-ASPARTIC ANHYDRIDE |
Article Data: | 24 |
Molecular Structure: | |
Formula: | C12H11NO5 |
Molecular Weight: | 249.223 |
Synonyms: | Asparticanhydride, N-carboxy-, N-benzyl ester, L- (8CI);Carbamic acid, (tetrahydro-2,5-dioxo-3-furanyl)-,phenylmethyl ester, (S)-;N-(Benzyloxycarbonyl)-L-aspartic acid anhydride;N-(Benzyloxycarbonyl)-L-aspartic anhydride;N-(Benzyloxycarbonyl)asparticanhydride;N-Carbobenzoxy-L-aspartic acid anhydride;N-Carbobenzoxy-L-asparticanhydride; |
EINECS: | 224-838-3 |
Density: | 1.37 g/cm3 |
Melting Point: | 123-124 °C(lit.) |
Boiling Point: | 490.2 °C at 760 mmHg |
Flash Point: | 250.3 °C |
Appearance: | White Powder |
PSA: | 81.70000 |
LogP: | 1.14580 |
Conditions | Yield |
---|---|
100% | |
With dicyclohexyl-carbodiimide In ethyl acetate 1.) 1 h, 0 deg C, 2.) 24 h, r.t.; | 98% |
With acetic anhydride for 0.0166667h; microwave irradiation; | 98% |
N-Cbz-L-Asp
A
benzyl N-[(3R)-2,5-dioxotetrahydrofuran-3-yl]carbamate
B
N-benzyloxycarbonyl-L-aspartic acid anhydride
Conditions | Yield |
---|---|
With acetic anhydride at 20 - 45℃; for 2.25h; Product distribution; Further Variations:; Reagents; Solvents; Temperatures; |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 89 percent 2: 98 percent / dicyclohexylcarbodiimide / ethyl acetate / 1.) 1 h, 0 deg C, 2.) 24 h, r.t. View Scheme | |
Multi-step reaction with 2 steps 1: K2CO3 / H2O / Ambient temperature 2: Ac2O / acetic acid / Ambient temperature View Scheme | |
Multi-step reaction with 2 steps 1: K2CO3 / H2O 2: Ac2O / acetic acid View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: toluene / anfangs unter Kuehlung 2: MgO; water; diethyl ether 3: acetic acid anhydride View Scheme |
Conditions | Yield |
---|---|
With triethylamine In dichloromethane for 12h; | 97% |
With triethylamine In dichloromethane for 12h; | 97% |
N-benzyloxycarbonyl-L-aspartic acid anhydride
benzyl (3S)-5-oxotetrahydro-3-furanylcarbamate
Conditions | Yield |
---|---|
With sodium tetrahydroborate In tetrahydrofuran | 91% |
With sodium tetrahydroborate at 0℃; for 3h; | 91% |
With sodium tetrahydroborate | 86% |
aniline
N-benzyloxycarbonyl-L-aspartic acid anhydride
benzyloxycarbonyl-L-aspartic acid dianilide
Conditions | Yield |
---|---|
Stage #1: N-benzyloxycarbonyl-L-aspartic acid anhydride In dimethyl sulfoxide at 20℃; for 3h; Stage #2: aniline With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In N,N-dimethyl-formamide at 20℃; for 24h; | 87% |
Stage #1: N-benzyloxycarbonyl-L-aspartic acid anhydride In N,N-dimethyl-formamide at 20℃; for 3h; Stage #2: aniline With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In N,N-dimethyl-formamide at 20℃; for 24h; | 87% |
3-methyl-1,2,4-thiadiazol-5-amine
N-benzyloxycarbonyl-L-aspartic acid anhydride
2-benzyloxycarbonylamino-N-(3-methyl-[1,2,4]thiadiazol-5-yl)-succinamic acid
Conditions | Yield |
---|---|
In dimethyl sulfoxide at 20℃; for 2h; | 85% |
Conditions | Yield |
---|---|
at 90℃; for 3.5h; | 82% |
at 90℃; for 3.5h; | 72% |
ethanol
N-benzyloxycarbonyl-L-aspartic acid anhydride
(S)-3-(benzyloxycarbonylamino)-4-ethoxy-4-oxobutanoic acid
Conditions | Yield |
---|---|
at 20℃; for 36h; | 81% |
Heating; | |
With N-cyclohexyl-cyclohexanamine In diethyl ether | |
for 18h; Product distribution / selectivity; Heating / reflux; |
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Molecular Structure of (S)-Benzyl (tetrahydro-2,5-dioxo-3-furyl)carbamate (CAS NO.4515-23-5):
IUPAC Name: benzyl N-(2,5-dioxooxolan-3-yl)carbamate
Empirical Formula: C12H11NO5
Molecular Weight: 249.2194
H bond acceptors: 6
H bond donors: 1
Freely Rotating Bonds: 4
Polar Surface Area: 72.91 Å2
Index of Refraction: 1.57
Molar Refractivity: 59.95 cm3
Molar Volume: 181.8 cm3
Surface Tension: 55.7 dyne/cm
Density: 1.37 g/cm3
Flash Point: 250.3 °C
Enthalpy of Vaporization: 75.67 kJ/mol
Boiling Point: 490.2 °C at 760 mmHg
Vapour Pressure: 9.31E-10 mmHg at 25°C
Melting Point: 123-124 °C(lit.)
InChI
InChI=1/C12H11NO5/c14-10-6-9(11(15)18-10)13-12(16)17-7-8-4-2-1-3-5-8/h1-5,9H,6-7H2,(H,13,16)
Smiles
O1C([C@@H](NC(=O)OCc2ccccc2)CC1=O)=O
EINECS: 224-838-3
Product Categories: N-CBZ; Aspartic Acid Derivatives; Peptide Synthesis; Unnatural Amino Acid Derivatives
WGK Germany: 3
(S)-Benzyl (tetrahydro-2,5-dioxo-3-furyl)carbamate , with CAS number of 4515-23-5, can be called N-Carbobenzyloxy-l-aspartic anhydride ; n-cbz-l-aspartic anhydride ; (s)-2-benzyloxycarbamylsuccinic anhydride ; (S)-benzyl (tetrahydro-2,5-dioxo-3-furyl)carbamate;N-Z-L-aspartic anhydride, 95% ; Carbamic acid, [(3S)-tetrahydro-2,5-dioxo-3-furanyl]-, phenylmethyl ester (9CI) ; (2,5-Dioxotetrahydrofuran-3β-yl)carbamic acid benzyl ester ; (2S)-2-(Benzyloxycarbonylamino)succinic anhydride .