1-hydroxy-pyrrolidine-2,5-dione
benzyl chloroformate
N-(Benzyloxycarbonyloxy)succinimide
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In water; ethyl acetate at 15℃; for 19h; Large scale; | 90.5% |
With TEA In 1,2-dimethoxyethane | 25% |
With triethylamine In acetonitrile at 5℃; for 1h; |
dicyclohexylamine salt of N-hydroxysuccinimide
benzyl chloroformate
N-(Benzyloxycarbonyloxy)succinimide
Conditions | Yield |
---|---|
In chloroform | 90% |
succinic acid anhydride
benzyl chloroformate
N-(Benzyloxycarbonyloxy)succinimide
Conditions | Yield |
---|---|
Stage #1: succinic acid anhydride With hydroxylamine sulfate In water Alkaline conditions; Stage #2: With phosphoric acid In water; toluene Reflux; Alkaline conditions; Stage #3: benzyl chloroformate In toluene for 2h; Reagent/catalyst; | 52.7% |
di(succinimido) carbonate
benzyl alcohol
N-(Benzyloxycarbonyloxy)succinimide
Conditions | Yield |
---|---|
With triethylamine In acetonitrile at 20℃; Substitution; | |
With triethylamine In acetonitrile at 20℃; for 0.75 - 1h; Product distribution / selectivity; |
N-cyclohexyl-cyclohexanamine
N-(Benzyloxycarbonyloxy)succinimide
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 95 percent / acetone 2: 90 percent / CHCl3 View Scheme |
N-(Benzyloxycarbonyloxy)succinimide
5-Carbamimidoyl-1H-indole-2-carboxylic acid ethyl ester
5-(Benzyloxycarbonylamino-imino-methyl)-1H-indole-2-carboxylic acid ethyl ester
Conditions | Yield |
---|---|
With triethylamine In N,N-dimethyl-formamide Ambient temperature; | 100% |
N-(Benzyloxycarbonyloxy)succinimide
ethanolamine
benzyl 2-hydroxyethylcarbamate
Conditions | Yield |
---|---|
With sodium carbonate In water; acetone at 20℃; for 4h; | 100% |
With TEA In tetrahydrofuran for 5h; | 92% |
In 1,4-dioxane; water for 12h; | 89% |
N-(Benzyloxycarbonyloxy)succinimide
5-hydroxypentylamine
5-<(benzyloxycarbonyl)amino>pentanol
Conditions | Yield |
---|---|
With sodium hydroxide In water; acetone at 20℃; for 4h; | 100% |
In tetrahydrofuran at 20℃; for 19h; Acylation; |
N-(Benzyloxycarbonyloxy)succinimide
(2S)-2-(2-methoxyethyl)piperidine
benzyl (2S)-2-(2-hydroxyethyl)piperidine-1-carboxylate
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 23℃; for 18h; | 100% |
N-(Benzyloxycarbonyloxy)succinimide
4-Aminobutanol
benzyl 4-hydroxybutylcarbamate
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In water; acetone at 20℃; for 4h; | 100% |
With triethylamine In acetone at 20℃; for 7h; | 92.8% |
N-(Benzyloxycarbonyloxy)succinimide
D-allylglycine
(R)-2-(benzyloxycarbonylamino)pent-4-enoic acid
Conditions | Yield |
---|---|
With water; triethylamine In 1,4-dioxane at 20℃; | 100% |
With triethylamine In tetrahydrofuran; water at 20℃; | 76% |
With sodium hydroxide; sodium hydrogencarbonate In 1,4-dioxane; water at 0℃; |
N-(Benzyloxycarbonyloxy)succinimide
L-allylglycine
(S)-2-(benzyloxycarbonylamino)pent-4-enoic acid
Conditions | Yield |
---|---|
With water; triethylamine In 1,4-dioxane | 100% |
Stage #1: N-(Benzyloxycarbonyloxy)succinimide; L-allylglycine With sodium hydroxide In water; acetone Stage #2: With sodium hydrogencarbonate In water; acetone for 20h; | 95% |
With sodium hydroxide; sodium hydrogencarbonate In 1,4-dioxane; water at 0℃; |
N-(Benzyloxycarbonyloxy)succinimide
(2R,1'S,3S,4S)-Nα-Boc-3,4-(Z-aminomethano)prolinol
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In water; acetone for 3h; | 100% |
4-[(3-amino-2-hydroxypropyl)oxy]benzonitrile
N-(Benzyloxycarbonyloxy)succinimide
Conditions | Yield |
---|---|
With triethylamine In chloroform at 0 - 20℃; | 100% |
N-(Benzyloxycarbonyloxy)succinimide
L-tert-Leucine
(S)-N-carbobenzoxy-tert-butylleucine
Conditions | Yield |
---|---|
With triethylamine In methanol at 20℃; for 14h; | 100% |
1,2,3,6-tetrahydropyridine
N-(Benzyloxycarbonyloxy)succinimide
1-benzyloxycarbonyl-1,2,3,6-tetrahydropyridine
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 20℃; | 100% |
With triethylamine In dichloromethane at 20 - 30℃; for 16h; |
N-(Benzyloxycarbonyloxy)succinimide
tert-butyl 3-(aminomethyl)-4-hydroxypyrrolidine-1-carboxylate
1,1-dimethylethyl 3-hydroxy-4-[({[(phenylmethyl)oxy]carbonyl}amino)methyl]-1-pyrrolidinecarboxylate
Conditions | Yield |
---|---|
In dichloromethane at 0℃; for 1h; | 100% |
N-(Benzyloxycarbonyloxy)succinimide
3-methyl-piperazine-1-carboxylic acid tert-butyl ester
O-benzyl carbamate
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In dichloromethane; water | 100% |
N-(Benzyloxycarbonyloxy)succinimide
(S)-methyl pipecolinate hydrochloride
(S)-1-(Benzyloxycarbonyl)-2-piperidine-carboxylic Acid Methyl Ester
Conditions | Yield |
---|---|
In dichloromethane (DCM); hexane; ethyl acetate | 100% |
N-(Benzyloxycarbonyloxy)succinimide
2-amino-2-methylpropanesulfonic acid sodium salt
sodium 2-(benzyloxycarbonylamino)-2-methylpropane-1-sulfonate
Conditions | Yield |
---|---|
In tetrahydrofuran; water at 20℃; for 16h; | 100% |
N-(Benzyloxycarbonyloxy)succinimide
1,3,2',6'-tetra-N-benzyloxycarbonyl-3',4'-dideoxy-2-hydroxyneamine
Conditions | Yield |
---|---|
With triethylamine In 1,2-dimethoxyethane; water at 45℃; Product distribution / selectivity; | 100% |
N-(Benzyloxycarbonyloxy)succinimide
1,4,7,10-tetraazacyclododecan
1,4,7,10-tetraaza-cyclododecane-1,7-dicarboxylic acid dibenzyl ester
Conditions | Yield |
---|---|
In chloroform at 20℃; for 48h; | 100% |
In chloroform at 20℃; for 0.5h; Inert atmosphere; | 100% |
In chloroform at 20℃; for 48h; |
N-(Benzyloxycarbonyloxy)succinimide
tert-butyl (3R,4R)-N-tert-butyloxycarbonyl-4-aminopyrrolidine-3-carboxylate
(3R,4R)-di-tert-butyl 4-(benzyloxycarbonylamino)pyrrolidine-1,3-dicarboxylate
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 3h; | 100% |
Conditions | Yield |
---|---|
With 4-methyl-morpholine In dichloromethane at 0 - 20℃; | 100% |
N-(Benzyloxycarbonyloxy)succinimide
3,3'-Diamino-N-methyldipropylamine
C23H31N3O4
Conditions | Yield |
---|---|
In chloroform at 20℃; for 16h; | 100% |
In chloroform at 20℃; for 16h; | |
In chloroform at 20℃; for 16h; |
N-(Benzyloxycarbonyloxy)succinimide
N,N-dimethylethylenediamine
Conditions | Yield |
---|---|
In chloroform at 0 - 20℃; for 2h; Inert atmosphere; | 100% |
In chloroform at 0 - 20℃; for 2h; Inert atmosphere; |
N-(Benzyloxycarbonyloxy)succinimide
C30H51N3O5
(1S,2S,4S)-4-(2-carbamoyl-2-methylpropyl-carbamoyl)-2-hydroxy-1-{(S)-2-[4-methoxy-3-(3-methoxypropoxy)-benzyl]-3-methylbutyl}-5-methylhexyl-carbamic acid benzyl ester
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 20℃; for 1h; | 100% |
N-(Benzyloxycarbonyloxy)succinimide
Conditions | Yield |
---|---|
In dichloromethane for 48h; | 100% |
N-(Benzyloxycarbonyloxy)succinimide
Citrulline
Nα-benzyloxy-carbonyl-L-citrulline
Conditions | Yield |
---|---|
Stage #1: Citrulline With sodium hydrogencarbonate In water at 20℃; for 1h; Stage #2: N-(Benzyloxycarbonyloxy)succinimide In 1,2-dimethoxyethane; water at 20℃; | 100% |
N-(Benzyloxycarbonyloxy)succinimide
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In water at 37℃; for 1h; Inert atmosphere; | 100% |
N-(Benzyloxycarbonyloxy)succinimide
(2S)-2-amino-3-(2-nitrophenyl)propanoic acid
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In water; acetonitrile at 20℃; | 100% |
N-(Benzyloxycarbonyloxy)succinimide
4-nitro-3-phenyl-L-alanine
(S)-2-(((benzyloxy)carbonyl)amino)-3-(4-nitrophenyl)propanoic acid
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In water; acetonitrile at 20℃; | 100% |
N-(Benzyloxycarbonyloxy)succinimide
(2S)-2-amino-3-(3-nitrophenyl)propanoic acid
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In water; acetonitrile at 20℃; | 100% |
Conditions | Yield |
---|---|
With sodium hydrogencarbonate at 20℃; | 100% |
With sodium hydrogencarbonate at 20℃; | 100% |
With sodium hydrogencarbonate at 20℃; | 100% |
N-(Benzyloxycarbonyloxy)succinimide
(1-(((benzyloxy)carbonyl)amino)-3-phenylpropyl)phosphinic acid
Conditions | Yield |
---|---|
With sodium carbonate In tetrahydrofuran; water at 0 - 20℃; for 24.25h; Inert atmosphere; | 100% |
The N-(Benzyloxycarbonyloxy)succinimide, with the cas registry number 13139-17-8, has the systematic name of 1-{[(benzyloxy)carbonyl]oxy}pyrrolidine-2,5-dione and the IUPAC name of benzyl (2,5-dioxopyrrolidin-1-yl) carbonate. This chemical is a kind of white crystal powde and it is sensitive.
The followings are the basic information of this chemical: Its product categories are various, including peptide coupling agents; amino acid derivatives; medical intermediates; imidazoles, pyrroles, pyrazoles, pyrrolidines; n-protecting reagents; biochemistry; condensation & active esterification; n-substituted maleimides, succinimides & phthalimides; n-substituted succinimides; peptide synthesis. As to its usage, it is usually used to be polypeptide reagent.
The characteristics of this chemical are as follows: (1)ACD/LogP: 0.42; (2)ACD/LogD (pH 5.5): 0.42; (3)ACD/LogD (pH 7.4): 0.42; (4)ACD/BCF (pH 5.5): 1.23; (5)ACD/BCF (pH 7.4): 1.23; (6)ACD/KOC (pH 5.5): 40.42; (7)ACD/KOC (pH 7.4): 40.42; (8)#H bond acceptors: 6; (9)#Freely Rotating Bonds: 5; (10)Polar Surface Area: 72.91; (11)Index of Refraction: 1.583; (12)Molar Refractivity: 60.2 cm3; (13)Molar Volume: 180 cm3; (14)Polarizability: 23.86 ×10-24 cm3; (15)Surface Tension: 58 dyne/cm; (16)Density: 1.38 g/cm3; (17)Flash Point: 177 °C; (18)Enthalpy of Vaporization: 61.57 kJ/mol; (19)Boiling Point: 369 °C at 760 mmHg; (20)Vapour Pressure: 1.23E-05 mmHg at 25°C; (21)Exact Mass: 249.063722; (22)MonoIsotopic Mass: 249.063722; (23)Topological Polar Surface Area: 72.9; (24)Heavy Atom Count: 18; (25)Complexity: 332.
The production method is as below: carbonochloridic acid benzyl ester could react with dicyclohexylamine salt of N-hydroxysuccinimide to produce N-(Benzyloxycarbonyloxy)succinimide, with the following condition: solution: CHCl3; yield: 90%.
Use of N-(Benzyloxycarbonyloxy)succinimide is as below: N-(Benzyloxycarbonyloxy)succinimide could react with L-serine to produce N-benzyloxycarbonyl-L-serine, with the following condition: reagent:sodium bicarbonate; solution: H2O and acetone; yield: 92% .
When dealing with this chemical, you should be cautious and then take some measures to protect yourself. Being irritant to eyes, respiratory system and skin, it may cause inflammation to the skin or other mucous membranes, and it may cause sensitisation by skin contact. If by inhalation, in contact with skin or if swallowed, it will be very harmful. Therefore, you should take the following instructions. Wear suitable protective clothing and avoid contacting with skin and eyes. If in case of contacting with eyes, rinse immediately with plenty of water and seek medical advice. Then remember not to breathe dust while using .
Additionally, the following data information could be converted into the molecular structure:
(1)SMILES:O=C2N(OC(=O)OCc1ccccc1)C(=O)CC2
(2)InChI:InChI=1/C12H11NO5/c14-10-6-7-11(15)13(10)18-12(16)17-8-9-4-2-1-3-5-9/h1-5H,6-8H2
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