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Name	(S)-Benzyl (tetrahydro-2,5-dioxo-3-furyl)carbamate	EINECS	224-838-3
CAS No.	4515-23-5	Density	1.37 g/cm³
PSA	81.70000	LogP	1.14580
Solubility	N/A	Melting Point	123-124 °C(lit.)
Formula	C₁₂H₁₁NO₅	Boiling Point	490.2 °C at 760 mmHg
Molecular Weight	249.223	Flash Point	250.3 °C
Transport Information	N/A	Appearance	White Powder
Safety		Risk Codes	N/A
Molecular Structure		Hazard Symbols	N/A
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;	Article Data	24

(S)-Benzyl (tetrahydro-2,5-dioxo-3-furyl)carbamate Synthetic route

: 1152-61-0
N-Cbz-L-Asp

: 4515-23-5
N-benzyloxycarbonyl-L-aspartic acid anhydride

Conditions

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%

: 1152-61-0
N-Cbz-L-Asp

A: 75443-62-8
benzyl N-[(3R)-2,5-dioxotetrahydrofuran-3-yl]carbamate

B: 4515-23-5
N-benzyloxycarbonyl-L-aspartic acid anhydride

Conditions

Conditions	Yield
With acetic anhydride at 20 - 45℃; for 2.25h; Product distribution; Further Variations:; Reagents; Solvents; Temperatures;

: 501-53-1
benzyl chloroformate

: 4515-23-5
N-benzyloxycarbonyl-L-aspartic acid anhydride

Conditions

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

: 100-51-6
benzyl alcohol

: 4515-23-5
N-benzyloxycarbonyl-L-aspartic acid anhydride

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: toluene / anfangs unter Kuehlung 2: MgO; water; diethyl ether 3: acetic acid anhydride View Scheme

: 124-22-1
n-Dodecylamine

: 4515-23-5
N-benzyloxycarbonyl-L-aspartic acid anhydride

: N-dodecyl-2-carbobenzyloxyaminosuccinamic acid

Conditions

Conditions	Yield
With triethylamine In dichloromethane for 12h;	97%
With triethylamine In dichloromethane for 12h;	97%

: 4515-23-5
N-benzyloxycarbonyl-L-aspartic acid anhydride

: 87219-29-2
benzyl (3S)-5-oxotetrahydro-3-furanylcarbamate

Conditions

Conditions	Yield
With sodium tetrahydroborate In tetrahydrofuran	91%
With sodium tetrahydroborate at 0℃; for 3h;	91%
With sodium tetrahydroborate	86%

: 62-53-3
aniline

: 4515-23-5
N-benzyloxycarbonyl-L-aspartic acid anhydride

: 685139-81-5
benzyloxycarbonyl-L-aspartic acid dianilide

Conditions

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%

: 17467-35-5
3-methyl-1,2,4-thiadiazol-5-amine

: 4515-23-5
N-benzyloxycarbonyl-L-aspartic acid anhydride

: 403736-43-6
2-benzyloxycarbonylamino-N-(3-methyl-[1,2,4]thiadiazol-5-yl)-succinamic acid

Conditions

Conditions	Yield
In dimethyl sulfoxide at 20℃; for 2h;	85%

: 100-51-6
benzyl alcohol

: 4515-23-5
N-benzyloxycarbonyl-L-aspartic acid anhydride

: 4779-31-1
Z-Asp-OBn

Conditions

Conditions	Yield
at 90℃; for 3.5h;	82%
at 90℃; for 3.5h;	72%

: 64-17-5
ethanol

: 4515-23-5
N-benzyloxycarbonyl-L-aspartic acid anhydride

: 4668-43-3
(S)-3-(benzyloxycarbonylamino)-4-ethoxy-4-oxobutanoic acid

Conditions

Conditions	Yield
at 20℃; for 36h;	81%
Heating;
With N-cyclohexyl-cyclohexanamine In diethyl ether
for 18h; Product distribution / selectivity; Heating / reflux;

(S)-Benzyl (tetrahydro-2,5-dioxo-3-furyl)carbamate Chemical Properties

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

(S)-Benzyl (tetrahydro-2,5-dioxo-3-furyl)carbamate Safety Profile

WGK Germany: 3

(S)-Benzyl (tetrahydro-2,5-dioxo-3-furyl)carbamate Specification

(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 .

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