N-Benzyloxycarbonyl-L-asparagine supplier

Name
N-Benzyloxycarbonyl-L-asparagine
EINECS 218-969-5
CAS No. 2304-96-3
Article Data33
CAS DataBase
Density 1.355 g/cm³
Solubility
Melting Point 160-165 °C
Formula C₁₂H₁₄N₂O₅
Boiling Point 580.6 °C at 760 mmHg
Molecular Weight 266.254
Flash Point 304.9 °C
Transport Information
Appearance white to light yellow crystal powder
Safety 24/25-36-26
Risk Codes 20/21/22-36/37/38
Molecular Structure
Hazard Symbols Xi,Xn
Synonyms Z-Asn-OH;Asparagine,N2-carboxy-, N-benzyl ester (6CI,7CI);Asparagine, N2-carboxy-, N2-benzylester, L- (8CI);Carbobenzoxy-L-asparagine;N2-(Benzyloxycarbonyl)-L-asparagine;NSC 59837;NSC 88498;
PSA 118.72000
LogP 1.33260

Synthetic route

: 25456-85-3
(S)-N-benzyloxycarbonylaspargine t-butyl ester

: 2304-96-3
N-benzyloxycarbonyl-L-asparagine

Conditions

Conditions	Yield
With triethylsilane; trifluoroacetic acid In dichloromethane for 0.583333h; Ambient temperature;	98%

: 70-47-3
L-asparagine

: dimethylsulfonium methyl sulfate

: 2304-96-3
N-benzyloxycarbonyl-L-asparagine

Conditions

Conditions	Yield
With triethylamine In water Ambient temperature;	95%

: 70-47-3
L-asparagine

: 501-53-1
benzyl chloroformate

: 2304-96-3
N-benzyloxycarbonyl-L-asparagine

Conditions

Conditions	Yield
With sodium carbonate In water	85%
With sodium carbonate In 1,4-dioxane; water at 20℃; Substitution;	84%
With sodium carbonate In 1,4-dioxane at 0 - 20℃; Inert atmosphere;	84%

: (S)-2-Benzyloxycarbonylamino-succinamic acid 3-methyl-but-2-enyl ester

: 2304-96-3
N-benzyloxycarbonyl-L-asparagine

Conditions

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate In dichloromethane at 20℃;	83%

: 160348-01-6
N-benzyloxycarbonyl-D,L-asparagine methyl ester

A: 2304-96-3
N-benzyloxycarbonyl-L-asparagine

B: 160348-02-7
N-benzyloxycarbonyl-D-asparagine methyl ester

Conditions

Conditions	Yield
With sodium hydroxide; Alcalase 2.4L from Bacillus sp; sodium chloride In tetrahydrofuran; phosphate buffer for 16h; pH=6.5;	A n/a B 46%
With sodium hydroxide; Alcalase 2.4L from Bacillus sp; sodium chloride In tetrahydrofuran; phosphate buffer for 2.1h; pH=6.5;	A 44% B n/a

: 5241-58-7
L-Phenylalanine amide

: C19H21N5O5*H(1+)

A: C7H9N3O*H(1+)

B: 2304-96-3
N-benzyloxycarbonyl-L-asparagine

C: 129095-57-4, 129117-20-0, 17327-64-9
Z-Asn-Phe-NH2

Conditions

Conditions	Yield
With sodium chloride; calcium chloride; papain In N,N-dimethyl-formamide at 25℃; for 0.416667h; pH=8; aq. buffer; Enzymatic reaction;	A n/a B 30.2% C 6.1%

...Expand

: 70-47-3
L-asparagine

: 2304-96-3
N-benzyloxycarbonyl-L-asparagine

Conditions

Conditions	Yield
With sodium hydrogencarbonate; benzyl chloroformate

: 3479-47-8
Z-Asp(OBzl)-OH

: 2304-96-3
N-benzyloxycarbonyl-L-asparagine

Conditions

Conditions	Yield
With ammonia

: 29880-22-6
N-benzyloxy-carbonyl-DL-asparagine

: 2304-96-3
N-benzyloxycarbonyl-L-asparagine

Conditions

Conditions	Yield
With Cinchonin
Multi-step reaction with 2 steps 1: 91 percent / SOCl2 / 0.25 h / 0 °C 2: 44 percent / Alcalase 2.4L from Bacillus sp.; NaCl; NaOH / aq. phosphate buffer; tetrahydrofuran / 2.1 h / pH 6.5 View Scheme

: 3160-47-2
N-(benzyloxycarbonyl)-L-aspartic acid 4-methyl ester

: 2304-96-3
N-benzyloxycarbonyl-L-asparagine

Conditions

Conditions	Yield
With ammonia

: 20806-05-7
N-Benzyloxycarbonyl-L-asparaginsaeure-β-

: 2304-96-3
N-benzyloxycarbonyl-L-asparagine

Conditions

Conditions	Yield
With trifluoroacetic acid

: 29880-22-6
N-benzyloxy-carbonyl-DL-asparagine

A: 4474-86-6
(R)-4-amino-2-(((benzyloxy)carbonyl)amino)-4-oxobutanoic acid

B: 2304-96-3
N-benzyloxycarbonyl-L-asparagine

Conditions

Conditions	Yield
resolved on CSP cellulose tris(3,5-dimethylphenylcarbamate) by chiral HPLC;

: 501-53-1
benzyl chloroformate

: 2304-96-3
N-benzyloxycarbonyl-L-asparagine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 90 percent / Et3N / acetonitrile / 2 h / 5 °C 2: 95 percent / Et3N / H2O / Ambient temperature View Scheme

: 100-51-6
benzyl alcohol

: 2304-96-3
N-benzyloxycarbonyl-L-asparagine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: toluene / anfangs unter Kuehlung 2: MgO; water / unter Kuehlung View Scheme

: 5241-60-1
di(phenylmethyl) (2S)-2-[(phenylmethoxy)carbonylamino]-butane-1,4-dioate

: 2304-96-3
N-benzyloxycarbonyl-L-asparagine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: aqueous dioxane; aqueous NaOH 2: liquid NH3 View Scheme

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

: 2304-96-3
N-benzyloxycarbonyl-L-asparagine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: toluene 2: aqueous dioxane; aqueous NaOH 3: liquid NH3 View Scheme

: 501-53-1
benzyl chloroformate

aqueous alanine: aqueous alanine

: 2304-96-3
N-benzyloxycarbonyl-L-asparagine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: aq. NaHCO3 2: liq. NH3 View Scheme

: 4779-31-1
Z-Asp-OBn

: 2304-96-3
N-benzyloxycarbonyl-L-asparagine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: (i) diethyl-prop-1-ynyl-amine, THF, (ii) aq. NaOH, dioxane 2: CF3CO2H View Scheme

: 67-56-1
methanol

: 2304-96-3
N-benzyloxycarbonyl-L-asparagine

: 4668-37-5
N-(benzyloxycarbonyl)asparagine methyl ester

Conditions

Conditions	Yield
With acetyl chloride at -15℃;	99%
With acetyl chloride at -15℃; for 24h;	98%
With thionyl chloride at 0℃; for 0.25h;	97%

: 2304-96-3
N-benzyloxycarbonyl-L-asparagine

: 59760-01-9, 76497-31-9, 46961-70-0
(S)-2-oxo-imidazolidine-1,5-dicarboxylic acid 1-benzyl ester

Conditions

Conditions	Yield
With sodium hydroxide; bromine In water at 55℃; for 3h; Hofmann rearrangement;	99%
With sodium hydroxide; bromine In water at 55℃; for 3h;	92%
With hypobromous acid	83%

: 16874-17-2
L-phenylalanine tert-butyl ester

: 2304-96-3
N-benzyloxycarbonyl-L-asparagine

: 21467-13-0
2-(2-benzyloxycarbonylamino-3-carbamoylpropionylamino)-3-phenylpropionic acid tert-butyl ester

Conditions

Conditions	Yield
With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 2h;	98%

: 2304-96-3
N-benzyloxycarbonyl-L-asparagine

: 5680-79-5
glycine ethyl ester hydrochloride

: 329257-17-2
N2-(carboxybenzyl)-L-asparaginylglycine methyl ester

Conditions

Conditions	Yield
With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere; Darkness;	98%

: 2304-96-3
N-benzyloxycarbonyl-L-asparagine

: 100-51-6
benzyl alcohol

: 82215-18-7
(S)-benzyl 2-(((benzyloxy)carbonyl)amino)-3-cyanopropanoate

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 12h; Inert atmosphere;	95%

: 2304-96-3
N-benzyloxycarbonyl-L-asparagine

: 35761-26-3
(S)-3-amino-2-(((benzyloxy)carbonyl)amino)propanoic acid

Conditions

Conditions	Yield
With [bis(acetoxy)iodo]benzene In water; ethyl acetate; acetonitrile at 20℃; for 4h; Hoffmann rearrangement;	93%
With [bis(acetoxy)iodo]benzene Hofmann rearrangement;	92%
With [bis(acetoxy)iodo]benzene In water; ethyl acetate; acetonitrile Hoffmann degradation;	92%

: 41444-88-6
L-glutamine tert-butyl ester

: 2304-96-3
N-benzyloxycarbonyl-L-asparagine

: 65895-51-4
Z-Asn-Gln-OBut

Conditions

Conditions	Yield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;	93%

: 67-56-1
methanol

: 2304-96-3
N-benzyloxycarbonyl-L-asparagine

: benzyl N-(2-carbamoyl-1-methoxyethyl)carbamate

Conditions

Conditions	Yield
With 3-(1-piperidino)propyl-functionalized silica gel at 10℃; Hofer-Moest reaction; Electrolysis;	93%

: 2304-96-3
N-benzyloxycarbonyl-L-asparagine

: 3309-41-9
N-(benzyloxycarbonyl)-3-cyano-L-alanine

Conditions

Conditions	Yield
With pyridine; trifluoroacetic anhydride In tetrahydrofuran at -10 - 20℃; for 15h;	92%
With pyridine; p-toluenesulfonyl chloride
With pyridine; acetic anhydride

: 2304-96-3
N-benzyloxycarbonyl-L-asparagine

: 7524-50-7
methyl (2S)-2-amino-3-phenylpropanoate hydrochloride

: 4976-86-7
benzyloxycarbonylasparaginyl-phenylalanine methyl ester

Conditions

Conditions	Yield
With Sephadex G-50; triethylamine; bromelain In ethyl acetate at 37℃; for 7h;	90%
(i) carbonochloridic acid adamantan-1-yl ester, Et3N, THF, dioxane, (ii) /BRN= 3597948/; Multistep reaction;
With diphenyl phosphoryl azide; triethylamine

: 1080-06-4
L-Tyr-OMe

: 2304-96-3
N-benzyloxycarbonyl-L-asparagine

: 20898-06-0
Cbz-L-Asn-L-Tyr-OMe

Conditions

Conditions	Yield
With Sephadex G-50; triethylamine; bromelain In ethyl acetate at 37℃; for 7h;	90%
With dicyclohexyl-carbodiimide

: 2304-96-3
N-benzyloxycarbonyl-L-asparagine

: 84552-42-1
H-Trp-Lys(Mtr)-Gly-OBut

: 84552-43-2
Z-Asn-Trp-Lys(Mtr)-Gly-OBut

Conditions

Conditions	Yield
With dicyclohexyl-carbodiimide; (3aR,4R,7S,7aS)-2-hydroxy-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindole-1,3(2H)-dione (N-hydroxy-5-exo-norbornene-2,3-dicarboximide) In N,N-dimethyl-formamide for 10h;	87.4%

: 684-93-5
1-methyl-1-nitrosourea

: 2304-96-3
N-benzyloxycarbonyl-L-asparagine

: 4668-37-5
N-(benzyloxycarbonyl)asparagine methyl ester

Conditions

Conditions	Yield
With sodium hydroxide In tetrahydrofuran; diethyl ether	86.76%

: 2304-96-3
N-benzyloxycarbonyl-L-asparagine

: 7517-19-3
methyl (L)-leucinate hydrochloride

: 14317-83-0
N-Benzyloxycarbonyl-L-asparaginyl-L-leucine Methyl Ester

Conditions

Conditions	Yield
With N-ethylmorpholine;; benzotriazol-1-ol In N,N-dimethyl-formamide 1) 2 h, -20 deg C, 2) 6 h, 0 deg C; overnight, r.t.;	84%
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 0 - 25℃;	50%
(i) 2-ethyl-5-(3-sulfo-phenyl)-isoxazolium betaine, (ii) /BRN= 3595133/; Multistep reaction;
(i) 2-ethyl-5-(4-sulfo-phenyl)-isoxazolium betaine, Et3N, MeNO2, (ii) /BRN= 3595133/, aq. NaOH; Multistep reaction;

: 2304-96-3
N-benzyloxycarbonyl-L-asparagine

: 728-87-0
4,4'-Dimethoxybenzhydrol

: 28252-50-8
Nα-Cbz-Nγ-(4,4'-dimethoxybenzhydryl)-Asn-OH

Conditions

Conditions	Yield
With sulfuric acid; acetic acid at 25℃; for 13.5h;	84%
With sulfuric acid In acetic acid

: 2304-96-3
N-benzyloxycarbonyl-L-asparagine

: 143224-64-0
N-<(3S-amino)-2R-hydroxy-4-phenylbutyl>-N'-(1,1-dimethylethyl)-N-(2-methyl-propyl)urea

: [1S-[1R*(R*),2S*]]-N1[3-[[[(1,1-dimethylethyl)amino]carbonyl](2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]-2-[(phenylmethylcarbamoyl)amino]butanediamide

Conditions

Conditions	Yield
Stage #1: N-benzyloxycarbonyl-L-asparagine With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In DMF (N,N-dimethyl-formamide) at 0℃; for 0.333333h; Stage #2: N-<(3S-amino)-2R-hydroxy-4-phenylbutyl>-N'-(1,1-dimethylethyl)-N-(2-methyl-propyl)urea In DMF (N,N-dimethyl-formamide) at 0 - 20℃; for 7h; Stage #3: With sodium hydrogencarbonate In DMF (N,N-dimethyl-formamide); water	83%

Yield

Stage #1: N-benzyloxycarbonyl-L-asparagine With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In DMF (N,N-dimethyl-formamide) at 0℃; for 0.333333h;
Stage #2: N-<(3S-amino)-2R-hydroxy-4-phenylbutyl>-N'-(1,1-dimethylethyl)-N-(2-methyl-propyl)urea In DMF (N,N-dimethyl-formamide) at 0 - 20℃; for 7h;
Stage #3: With sodium hydrogencarbonate In DMF (N,N-dimethyl-formamide); water

83%

: 7541-02-8
(Z)-2-(hydroxyimino)-2-phenylacetonitrile

: 2304-96-3
N-benzyloxycarbonyl-L-asparagine

: 126706-95-4
C20H18N4O5

Conditions

Conditions	Yield
With dicyclohexyl-carbodiimide In ethyl acetate other solvent, 1. 0 deg C 1 h 2. rt 1 h;	82%
With 4-methyl-morpholine; isobutyl chloroformate In tetrahydrofuran 1.) 10 min, -15 deg C 2.) 1 h, -15 deg C 3.) 1 h, rt;

: 2304-96-3
N-benzyloxycarbonyl-L-asparagine

: 13518-40-6
L-valine tert-butylester hydrochloride

: 26061-17-6
N-(benzyloxycarbonyl)-L-asparaginyl-L-valine tert-butyl ester

Conditions

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane; d7-N,N-dimethylformamide at 0℃; for 3h;	82%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane; N,N-dimethyl-formamide at 0℃; for 3h;	81%

: 2304-96-3
N-benzyloxycarbonyl-L-asparagine

: 690223-68-8
(-)-(3S,4aS,8aS,2'R,3'R)-[3'-amino-2'-hydroxy-3'-(thiophen-2-yl)-propyl]-decahydro-isoquinoline-3-carboxylic acid tert-butylamide

: (-)-(3S,4aS,8aS,2'R,3'R)-{1-[3-(3-tert-butyl-carbamoyl-decahydro-isoquinolin-2-yl)-2-hydroxy-1-thiophen-2-yl-propylcarbamoyl]-2-carbamoyl-ethyl}-carbamic acid bezyl ester

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 6h;	80%

: 2304-96-3
N-benzyloxycarbonyl-L-asparagine

: HCl*H-Ile-Leu-Aib-OMe

: Z-Asn-Ile-Leu-Aib-OMe

Conditions

Conditions	Yield
With TEA; benzotriazol-1-ol; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide for 34h; Ambient temperature;	78%

: 2304-96-3
N-benzyloxycarbonyl-L-asparagine

: 106-95-6
allyl bromide

: 848047-83-6
(S)-2-((benzyloxycarbonyl)amino)succinic acid 1-allyl ester 4-amide

Conditions

Conditions	Yield
With sodium iodide In N,N-dimethyl-formamide for 24h;	78%
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 20℃; for 48h;	68%
With sodium iodide In N,N-dimethyl-formamide at 20℃; for 24h;	57%

: 40846-98-8, 108258-30-6
L-glutamine methyl ester

: 2304-96-3
N-benzyloxycarbonyl-L-asparagine

: 16305-90-1
(S)-2-((S)-2-Benzyloxycarbonylamino-3-carbamoyl-propionylamino)-4-carbamoyl-butyric acid methyl ester

Conditions

Conditions	Yield
With 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine; 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 0 - 20℃; for 10h;	78%

: 2304-96-3
N-benzyloxycarbonyl-L-asparagine

: 5132-46-7
H-Gln-O-But

: 65895-51-4
Z-Asn-Gln-OBut

Conditions

Conditions	Yield
With TEA; dicyclohexyl-carbodiimide; (3aR,4R,7S,7aS)-2-hydroxy-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindole-1,3(2H)-dione (N-hydroxy-5-exo-norbornene-2,3-dicarboximide) In N,N-dimethyl-formamide for 15h;	77.8%

: 2304-96-3
N-benzyloxycarbonyl-L-asparagine

: 100-39-0
benzyl bromide

: 4668-39-7
benzyl Nα-benzyloxycarbonyl-L-asparaginate

Conditions

Conditions	Yield
Stage #1: N-benzyloxycarbonyl-L-asparagine With caesium carbonate In methanol; water pH=7; Stage #2: benzyl bromide In N,N-dimethyl-formamide at 20℃; for 6h;	76%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 3h;

: 2304-96-3
N-benzyloxycarbonyl-L-asparagine

: 51537-21-4
O-tert-butyl-L-serine tert-butyl ester hydrochloride

: 26055-00-5
N-carbobenzyloxy-L-asparaginyl-O-tert-butyl-L-serine tert-butyl ester

Conditions

Conditions	Yield
With diethyl cyanophosphonate; triethylamine In N,N-dimethyl-formamide	75%

: 108-20-3
di-isopropyl ether

: 5440-76-6
(4-methylphenyl)diphenylmethanol

: 2304-96-3
N-benzyloxycarbonyl-L-asparagine

: Z-Asn(Mtt)-OH

Conditions

Conditions	Yield
With sulfuric acid; acetic anhydride; acetic acid In water; ethyl acetate	75%

...Expand

N-Benzyloxycarbonyl-L-asparagine Specification

The N-Benzyloxycarbonyl-L-asparagine, with the CAS registry number 2304-96-3, is also known as Carbobenzoxy-L-asparagine. It belongs to the product categories of Chiral; Amino Acid Derivatives; Protected Amino Acid & Peptides; Asparagine [Asn, N]; Z-Amino Acids and Derivatives; Amino Acids; Amino Acids (N-Protected); Biochemistry; Cbz-Amino Acids; Chiral Compounds; Z-Amino Acid Series. Its EINECS registry number is 218-969-5. This chemical's molecular formula is C₁₂H₁₄N₂O₅ and molecular weight is 266.25. Its IUPAC name is called 4-amino-4-oxo-2-(phenylmethoxycarbonylamino)butanoic acid. This chemical is white to light yellow crystal powder. The product should be sealed and stored in cool, dry place.

Physical properties of N-Benzyloxycarbonyl-L-asparagine: (1)ACD/LogP: 0.89; (2)ACD/LogD (pH 5.5): -1.3; (3)ACD/LogD (pH 7.4): -2.7; (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: 7; (9)#H bond donors: 4; (10)#Freely Rotating Bonds: 7; (11)Index of Refraction: 1.573; (12)Molar Refractivity: 64.79 cm³; (13)Molar Volume: 196.3 cm³; (14)Surface Tension: 61 dyne/cm; (15)Density: 1.355 g/cm³; (16)Flash Point: 304.9 °C; (17)Enthalpy of Vaporization: 91.34 kJ/mol; (18)Boiling Point: 580.6 °C at 760 mmHg; (19)Vapour Pressure: 2.54E-14 mmHg at 25°C.

When you are using this chemical, please be cautious about it as the following:
This chemical may cause damage to health. It is harmful by inhalation, in contact with skin and if swallowed. It is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. Whenever you will contact it, please wear suitable protective clothing. Finally, you must avoid contacting it with skin and eyes.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: C1=CC=C(C=C1)COC(=O)NC(CC(=O)N)C(=O)O
(2)InChI: InChI=1S/C12H14N2O5/c13-10(15)6-9(11(16)17)14-12(18)19-7-8-4-2-1-3-5-8/h1-5,9H,6-7H2,(H2,13,15)(H,14,18)(H,16,17)
(3)InChIKey: FUCKRCGERFLLHP-UHFFFAOYSA-N

Product Name

N-Benzyloxycarbonyl-L-asparagine

Synthetic route

N-Benzyloxycarbonyl-L-asparagine Specification

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