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inquiryProduct name Nalpha-Carbobenzyloxy-L-asparagine Alias N-Benzyloxycarbonyl-L-asparagine; Z-Asn-OH; Cbz-L-asparagine CAS NO 2304-96-3 EINECS No.
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inquiry(S)-N-benzyloxycarbonylaspargine t-butyl ester
N-benzyloxycarbonyl-L-asparagine
Conditions | Yield |
---|---|
With triethylsilane; trifluoroacetic acid In dichloromethane for 0.583333h; Ambient temperature; | 98% |
Conditions | Yield |
---|---|
With triethylamine In water Ambient temperature; | 95% |
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% |
N-benzyloxycarbonyl-L-asparagine
Conditions | Yield |
---|---|
With trimethylsilyl trifluoromethanesulfonate In dichloromethane at 20℃; | 83% |
N-benzyloxycarbonyl-D,L-asparagine methyl ester
A
N-benzyloxycarbonyl-L-asparagine
B
N-benzyloxycarbonyl-D-asparagine methyl ester
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 |
L-Phenylalanine amide
B
N-benzyloxycarbonyl-L-asparagine
C
Z-Asn-Phe-NH2
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% |
Conditions | Yield |
---|---|
With sodium hydrogencarbonate; benzyl chloroformate |
Conditions | Yield |
---|---|
With ammonia |
N-benzyloxy-carbonyl-DL-asparagine
N-benzyloxycarbonyl-L-asparagine
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 |
N-(benzyloxycarbonyl)-L-aspartic acid 4-methyl ester
N-benzyloxycarbonyl-L-asparagine
Conditions | Yield |
---|---|
With ammonia |
N-Benzyloxycarbonyl-L-asparaginsaeure-β-
N-benzyloxycarbonyl-L-asparagine
Conditions | Yield |
---|---|
With trifluoroacetic acid |
N-benzyloxy-carbonyl-DL-asparagine
A
(R)-4-amino-2-(((benzyloxy)carbonyl)amino)-4-oxobutanoic acid
B
N-benzyloxycarbonyl-L-asparagine
Conditions | Yield |
---|---|
resolved on CSP cellulose tris(3,5-dimethylphenylcarbamate) by chiral HPLC; |
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 |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: toluene / anfangs unter Kuehlung 2: MgO; water / unter Kuehlung View Scheme |
di(phenylmethyl) (2S)-2-[(phenylmethoxy)carbonylamino]-butane-1,4-dioate
N-benzyloxycarbonyl-L-asparagine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: aqueous dioxane; aqueous NaOH 2: liquid NH3 View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: toluene 2: aqueous dioxane; aqueous NaOH 3: liquid NH3 View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: aq. NaHCO3 2: liq. NH3 View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: (i) diethyl-prop-1-ynyl-amine, THF, (ii) aq. NaOH, dioxane 2: CF3CO2H View Scheme |
methanol
N-benzyloxycarbonyl-L-asparagine
N-(benzyloxycarbonyl)asparagine methyl ester
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% |
N-benzyloxycarbonyl-L-asparagine
(S)-2-oxo-imidazolidine-1,5-dicarboxylic acid 1-benzyl ester
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% |
L-phenylalanine tert-butyl ester
N-benzyloxycarbonyl-L-asparagine
2-(2-benzyloxycarbonylamino-3-carbamoylpropionylamino)-3-phenylpropionic acid tert-butyl ester
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% |
N-benzyloxycarbonyl-L-asparagine
glycine ethyl ester hydrochloride
N2-(carboxybenzyl)-L-asparaginylglycine methyl ester
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% |
N-benzyloxycarbonyl-L-asparagine
benzyl alcohol
(S)-benzyl 2-(((benzyloxy)carbonyl)amino)-3-cyanopropanoate
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 12h; Inert atmosphere; | 95% |
N-benzyloxycarbonyl-L-asparagine
(S)-3-amino-2-(((benzyloxy)carbonyl)amino)propanoic acid
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% |
L-glutamine tert-butyl ester
N-benzyloxycarbonyl-L-asparagine
Z-Asn-Gln-OBut
Conditions | Yield |
---|---|
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; | 93% |
Conditions | Yield |
---|---|
With 3-(1-piperidino)propyl-functionalized silica gel at 10℃; Hofer-Moest reaction; Electrolysis; | 93% |
Conditions | Yield |
---|---|
With pyridine; trifluoroacetic anhydride In tetrahydrofuran at -10 - 20℃; for 15h; | 92% |
With pyridine; p-toluenesulfonyl chloride | |
With pyridine; acetic anhydride |
N-benzyloxycarbonyl-L-asparagine
methyl (2S)-2-amino-3-phenylpropanoate hydrochloride
benzyloxycarbonylasparaginyl-phenylalanine methyl ester
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 |
Conditions | Yield |
---|---|
With Sephadex G-50; triethylamine; bromelain In ethyl acetate at 37℃; for 7h; | 90% |
With dicyclohexyl-carbodiimide |
N-benzyloxycarbonyl-L-asparagine
H-Trp-Lys(Mtr)-Gly-OBut
Z-Asn-Trp-Lys(Mtr)-Gly-OBut
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% |
1-methyl-1-nitrosourea
N-benzyloxycarbonyl-L-asparagine
N-(benzyloxycarbonyl)asparagine methyl ester
Conditions | Yield |
---|---|
With sodium hydroxide In tetrahydrofuran; diethyl ether | 86.76% |
N-benzyloxycarbonyl-L-asparagine
methyl (L)-leucinate hydrochloride
N-Benzyloxycarbonyl-L-asparaginyl-L-leucine Methyl Ester
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; |
N-benzyloxycarbonyl-L-asparagine
4,4'-Dimethoxybenzhydrol
Nα-Cbz-Nγ-(4,4'-dimethoxybenzhydryl)-Asn-OH
Conditions | Yield |
---|---|
With sulfuric acid; acetic acid at 25℃; for 13.5h; | 84% |
With sulfuric acid In acetic acid |
N-benzyloxycarbonyl-L-asparagine
N-<(3S-amino)-2R-hydroxy-4-phenylbutyl>-N'-(1,1-dimethylethyl)-N-(2-methyl-propyl)urea
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% |
(Z)-2-(hydroxyimino)-2-phenylacetonitrile
N-benzyloxycarbonyl-L-asparagine
C20H18N4O5
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; |
N-benzyloxycarbonyl-L-asparagine
L-valine tert-butylester hydrochloride
N-(benzyloxycarbonyl)-L-asparaginyl-L-valine tert-butyl ester
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% |
N-benzyloxycarbonyl-L-asparagine
(-)-(3S,4aS,8aS,2'R,3'R)-[3'-amino-2'-hydroxy-3'-(thiophen-2-yl)-propyl]-decahydro-isoquinoline-3-carboxylic acid tert-butylamide
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 6h; | 80% |
Conditions | Yield |
---|---|
With TEA; benzotriazol-1-ol; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide for 34h; Ambient temperature; | 78% |
N-benzyloxycarbonyl-L-asparagine
allyl bromide
(S)-2-((benzyloxycarbonyl)amino)succinic acid 1-allyl ester 4-amide
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% |
L-glutamine methyl ester
N-benzyloxycarbonyl-L-asparagine
(S)-2-((S)-2-Benzyloxycarbonylamino-3-carbamoyl-propionylamino)-4-carbamoyl-butyric acid methyl ester
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% |
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% |
N-benzyloxycarbonyl-L-asparagine
benzyl bromide
benzyl Nα-benzyloxycarbonyl-L-asparaginate
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; |
N-benzyloxycarbonyl-L-asparagine
O-tert-butyl-L-serine tert-butyl ester hydrochloride
N-carbobenzyloxy-L-asparaginyl-O-tert-butyl-L-serine tert-butyl ester
Conditions | Yield |
---|---|
With diethyl cyanophosphonate; triethylamine In N,N-dimethyl-formamide | 75% |
di-isopropyl ether
(4-methylphenyl)diphenylmethanol
N-benzyloxycarbonyl-L-asparagine
Conditions | Yield |
---|---|
With sulfuric acid; acetic anhydride; acetic acid In water; ethyl acetate | 75% |
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