1-hydroxy-pyrrolidine-2,5-dione
(fluorenylmethoxy)carbonyl chloride
N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
Conditions | Yield |
---|---|
With triethylamine In 1,4-dioxane for 1h; Ambient temperature; | 96% |
With sodium carbonate In water; toluene at 25 - 30℃; for 2h; Reagent/catalyst; Solvent; | 56.3% |
With sodium carbonate In water; acetone for 0.5h; Acylation; |
(fluorenylmethoxy)carbonyl chloride
dicyclohexylamine salt of N-hydroxysuccinimide
N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
Conditions | Yield |
---|---|
In chloroform | 90% |
(fluorenylmethoxy)carbonyl chloride
N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
Conditions | Yield |
---|---|
In chloroform | 90% |
2,5-dioxopyrrolidin-1-yl carbonochloridate
9-Fluorenylmethanol
N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
Conditions | Yield |
---|---|
With pyridine In dichloromethane for 5h; Ambient temperature; | 72% |
N-cyclohexyl-cyclohexanamine
N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 95 percent / acetone 2: 90 percent / CHCl3 View Scheme |
L-serin
N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
N-(9H-fluoren-9-ylmethoxycarbonyl)-L-serine
Conditions | Yield |
---|---|
With sodium hydrogencarbonate | 100% |
With sodium carbonate In 1,4-dioxane | 97% |
With sodium hydrogencarbonate In water; acetonitrile | 94% |
L-threonine
N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
Fmoc-Thr-OH
Conditions | Yield |
---|---|
With sodium hydrogencarbonate | 100% |
Stage #1: L-threonine; N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide With sodium carbonate In 1,4-dioxane; water at 20℃; Inert atmosphere; Stage #2: With hydrogenchloride In water pH=4; | 100% |
With sodium hydrogencarbonate In acetone | 97% |
methyl (2S)-2-amino-3-hydroxypropanoate hydrochloride
N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
N-[(9-fluorenylmethoxy)carbonyl]-L-serine methyl ester
Conditions | Yield |
---|---|
Stage #1: methyl (2S)-2-amino-3-hydroxypropanoate hydrochloride With sodium hydrogencarbonate In 1,4-dioxane; water at 20℃; for 0.25h; Stage #2: N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide In 1,4-dioxane; water at 20℃; for 14h; | 100% |
Stage #1: methyl (2S)-2-amino-3-hydroxypropanoate hydrochloride With sodium hydrogencarbonate In 1,4-dioxane; water at 20℃; for 0.25h; Stage #2: N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide In 1,4-dioxane; water at 20℃; for 14h; | 100% |
Stage #1: methyl (2S)-2-amino-3-hydroxypropanoate hydrochloride With sodium hydrogencarbonate In 1,4-dioxane at 20℃; for 0.5h; Stage #2: N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide In 1,4-dioxane at 20℃; for 24h; | 97% |
N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
3-(3-(amino-4-methoxyphenylmethyl)-4-methoxyphenyl)propionic acid
3-(α-fluoren-9-ylmethoxycarbonylamino-4-methoxybenzyl)-4-methoxyphenylpropionic acid
Conditions | Yield |
---|---|
With triethylamine In N,N-dimethyl-formamide for 1h; Ambient temperature; | 100% |
N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
AmBisome
3′-N-Fmoc-AmB
Conditions | Yield |
---|---|
With pyridine In N,N-dimethyl-formamide at 20℃; for 18h; | 100% |
With pyridine In methanol; N,N-dimethyl-formamide at 23℃; for 4h; | 99% |
With pyridine In methanol; N,N-dimethyl-formamide at 20℃; for 12h; | 95% |
N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In water; acetone for 12h; Ambient temperature; | 100% |
N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
(R)-2-Amino-3-(2-tert-butoxycarbonylamino-ethylsulfamoyl)-propionic acid
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In water; acetone for 12h; Ambient temperature; | 100% |
N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
(R)-2-Amino-4-(2-tert-butoxycarbonylamino-ethylsulfamoyl)-butyric acid
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In water; acetone for 12h; Ambient temperature; | 100% |
N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
Propargylamine
Fmoc-N-propargylamine
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 1h; Cooling with ice; | 100% |
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; | 100% |
With dmap In dichloromethane at 0 - 20℃; for 4h; | 94% |
Tyr(tBu)
N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
(S)-tert-butyl 2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(4-hydroxyphenyl)propanoate
Conditions | Yield |
---|---|
Stage #1: Tyr(tBu); N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide With sodium hydrogencarbonate In 1,4-dioxane; water at 20℃; for 18h; Stage #2: With hydrogenchloride; water In 1,4-dioxane | 100% |
With N-ethyl-N,N-diisopropylamine In acetone at 22 - 25℃; | 95.8% |
With N-ethyl-N,N-diisopropylamine In acetone at 20℃; for 12h; | 95.8% |
N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
(2S)-1,2,3,6-tetrahydropyridine-2-carboxylic acid
(S)-3,6-Dihydro-2H-pyridine-1,2-dicarboxylic acid 1-(9H-fluoren-9-ylmethyl) ester
Conditions | Yield |
---|---|
With sodium hydroxide; sodium hydrogencarbonate | 100% |
N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
(3R,6R,9S)-1-aza-9-carboxy-3-(9'-fluorenylmethoxycarbonylamino)-2-oxo-bicyclo[4.3.0]nonane
Conditions | Yield |
---|---|
Stage #1: (3S,6R,8aR)-6-Amino-5-oxo-octahydro-indolizine-3-carboxylic acid With trifluoroacetic acid In dichloromethane at 20℃; for 1h; Stage #2: N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide With sodium carbonate In tetrahydrofuran; water at 20℃; for 3h; Further stages.; | 100% |
N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
(2S,6R,9S)-2-oxo-3-(9-fluorenyloxycarbonylamino)-1-azabicyclo[4.2.0]nonane-9-carboxylic acid
Conditions | Yield |
---|---|
Stage #1: (3S,6S,8aR)-6-Amino-5-oxo-octahydro-indolizine-3-carboxylic acid With trifluoroacetic acid In dichloromethane at 20℃; for 1h; Stage #2: N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide With sodium carbonate In tetrahydrofuran; water at 20℃; for 3h; Further stages.; | 100% |
With sodium carbonate In 1,4-dioxane; water |
N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
(3R,6S,9S)-1-aza-9-carboxy-3-(9'-fluorenylmethoxycarbonylamino)-2-oxo-bicyclo[4.3.0]nonane
Conditions | Yield |
---|---|
Stage #1: (3S,6R,8aS)-6-Amino-5-oxo-octahydro-indolizine-3-carboxylic acid With trifluoroacetic acid In dichloromethane at 20℃; for 1h; Stage #2: N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide With sodium carbonate In tetrahydrofuran; water at 20℃; for 3h; Further stages.; | 100% |
N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
(3S,6S,8aS)-6-Amino-5-oxo-octahydro-indolizine-3-carboxylic acid
(3S,6S,9S)-2-oxo-3-(N-(9-fluorenylmethoxycarbonyl)amino)-1-azabicyclo[4.3.0]nonane-9-carboxylic acid
Conditions | Yield |
---|---|
Stage #1: (3S,6S,8aS)-6-Amino-5-oxo-octahydro-indolizine-3-carboxylic acid With trifluoroacetic acid In dichloromethane at 20℃; for 1h; Stage #2: N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide With sodium carbonate In tetrahydrofuran; water at 20℃; for 3h; Further stages.; | 100% |
With sodium carbonate In 1,4-dioxane; water | 265 mg |
N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
(3R,7R,10S)-1-aza-10-carboxy-3-(9'-fluorenylmethoxycarbonylamino)-2-oxo-bicyclo[5.3.0]decane
Conditions | Yield |
---|---|
Stage #1: (3S,6R,9aR)-6-Amino-5-oxo-octahydro-pyrrolo[1,2-a]azepine-3-carboxylic acid With trifluoroacetic acid In dichloromethane at 20℃; for 1h; Stage #2: N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide With sodium carbonate In tetrahydrofuran; water at 20℃; for 3h; Further stages.; | 100% |
N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
(3S,7R,10S)-2-oxo-3-N-(9-fluorenylmethyloxycarbonyl)amino-1-azabicyclo[5.3.0]decane-10-carboxylic acid
Conditions | Yield |
---|---|
Stage #1: (3S,6S,9aR)-6-Amino-5-oxo-octahydro-pyrrolo[1,2-a]azepine-3-carboxylic acid With trifluoroacetic acid In dichloromethane at 20℃; for 1h; Stage #2: N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide With sodium carbonate In tetrahydrofuran; water at 20℃; for 3h; Further stages.; | 100% |
N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
(3R,7S,10S)-1-aza-10-carboxy-3-(9'-fluorenylmethoxycarbonylamino)-2-oxo-bicyclo[5.3.0]decane
Conditions | Yield |
---|---|
Stage #1: (3S,6R,9aS)-6-Amino-5-oxo-octahydro-pyrrolo[1,2-a]azepine-3-carboxylic acid With trifluoroacetic acid In dichloromethane at 20℃; for 1h; Stage #2: N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide With sodium carbonate In tetrahydrofuran; water at 20℃; for 3h; Further stages.; | 100% |
N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
(3S,7S,10S)-2-oxo-3-N-(9-fluorenylmethyloxycarbonyl)amino-1-azabicyclo[5.3.0]decane-10-carboxylic acid
Conditions | Yield |
---|---|
Stage #1: (3S,6S,9aS)-6-Amino-5-oxo-octahydro-pyrrolo[1,2-a]azepine-3-carboxylic acid With trifluoroacetic acid In dichloromethane at 20℃; for 1h; Stage #2: N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide With sodium carbonate In tetrahydrofuran; water at 20℃; for 3h; Further stages.; | 100% |
N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
Conditions | Yield |
---|---|
With triethylamine In methanol | 100% |
(S)-2-amino-2-cyclopentylacetic acid
N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
Conditions | Yield |
---|---|
With sodium carbonate In 1,4-dioxane; water | 100% |
glycinamide hydrochloride
N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
Fmoc-Gly-NH2
Conditions | Yield |
---|---|
With sodium carbonate In acetone at 20℃; for 1h; | 100% |
With sodium hydrogencarbonate In acetone at 20℃; for 2h; pH=7; | 80% |
With sodium carbonate In water; acetone at 0 - 20℃; for 1.5h; | 72% |
N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
N-α-tert-butyloxycarbonyl-(2S,4R)-2-tert-butyloxycarbonylmethyl-4-(adenin-9'-yl)-pyrrolidine
N-α-9-fluorenylmethoxycarbonyl-(2S,4R)-2-hydroxycarbonylmethoxymethyl-4-(adenin-9'-yl)-pyrrolidine
Conditions | Yield |
---|---|
Stage #1: N-α-tert-butyloxycarbonyl-(2S,4R)-2-tert-butyloxycarbonylmethyl-4-(adenin-9'-yl)-pyrrolidine With hydrogen bromide; acetic acid at 20℃; for 1h; Stage #2: N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide With sodium hydrogencarbonate In acetonitrile at 20℃; | 100% |
N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
3-deoxy-3-(9-fluorenylmethoxycarbonyl)amino-1,2-O-isopropylidene-α-L-ribofuranose
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In water; acetone at 20℃; for 1h; | 100% |
N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
(2S,4S)-N-fluorenylmethoxycarbonyl-2-carboxy-4-diphenylphosphinothioyl-pyrrolidine
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In water; acetone | 100% |
4-Aminobutanol
N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
(9H-fluoren-9-yl)methyl (4-hydroxybutyl)carbamate
Conditions | Yield |
---|---|
With pyridine In methanol at 23℃; for 23h; | 100% |
In tetrahydrofuran; water at 20℃; Cooling with ice; | 1.21 g |
6-amino-1-hexanol
N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
(9H-fluoren-9-yl)methyl (6-hydroxyhexyl)carbamate
Conditions | Yield |
---|---|
With pyridine In methanol at 23℃; for 16h; | 100% |
With pyridine In methanol at 23℃; | |
With sodium carbonate In 1,4-dioxane; water at 20℃; for 0.5h; | 11 g |
N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In water; acetonitrile at 20℃; for 4h; | 100% |
N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In dichloromethane pH=9; | 100% |
N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
ethanolamine
N-(9-fluorenylmethoxycarbonyl)-2-aminoethanol
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In water; acetone at 20℃; for 4h; | 100% |
In 1,4-dioxane; water at 20℃; for 16h; | 97% |
With triethylamine In tetrahydrofuran at 20℃; | 93% |
The 9-Fluorenylmethyl succinimidyl carbonate, with the CAS registry number 82911-69-1, is also known as 2,5-Pyrrolidinedione, 1-(((9H-fluoren-9-ylmethoxy)carbonyl)oxy)-. It belongs to the product categories of Amino Acid Derivatives; Medical Intermediates; Benzocycles; Fluorenes, Flurenones; Pyrrolidines; N-Protecting Reagents; Biochemistry; Condensation & Active Esterification; Fluorenes; Fluorenes & Fluorenones; N-Substituted Maleimides, Succinimides & Phthalimides; N-Substituted Succinimides; Peptide Synthesis; Protective Reagents (Peptide Synthesis); Synthetic Organic Chemistry; Fmoc-Amino Acid Series. Its EINECS registry number is 433-520-5. This chemical's molecular formula is and molecular weight is . Its IUPAC name is called (2,5-dioxopyrrolidin-1-yl) 9H-fluoren-9-ylmethyl carbonate.
Physical properties of 9-Fluorenylmethyl succinimidyl carbonate: (1)ACD/LogP: 2.32; (2)ACD/LogD (pH 5.5): 2.32; (3)ACD/LogD (pH 7.4): 2.32; (4)ACD/BCF (pH 5.5): 33.91; (5)ACD/BCF (pH 7.4): 33.91; (6)ACD/KOC (pH 5.5): 433.51; (7)ACD/KOC (pH 7.4): 433.51; (8)#H bond acceptors: 6; (9)#Freely Rotating Bonds: 5; (10)Index of Refraction: 1.661; (11)Molar Refractivity: 87.47 cm3; (12)Molar Volume: 236.4 cm3; (13)Surface Tension: 66.7 dyne/cm; (14)Density: 1.42 g/cm3; (15)Flash Point: 252.7 °C; (16)Enthalpy of Vaporization: 76.16 kJ/mol; (17)Boiling Point: 494.3 °C at 760 mmHg; (18)Vapour Pressure: 6.55E-10 mmHg at 25°C.
Preparation: this chemical can be prepared by N-hydroxy-succinimide and 9H-fluoren-9-ylmethyl chloroformate. This reaction is a kind of Acylation. It will need reagent Na2CO3 and solvent H2O, acetone. The reaction time is 30 min.
Uses of 9-Fluorenylmethyl succinimidyl carbonate: it can be used to produce N-(9-fluorenylmethyloxycarbonyl)-L-serine methyl ester. This reaction will need reagent aq. sodium hydrogen carbonate and solvent dioxane with reaction time of 10 min. The yield is about 80%.
When you are using this chemical, please be cautious about it as the following:
This chemical may cause inflammation to the skin or other mucous membranes. 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, gloves and eye/face protection.
You can still convert the following datas into molecular structure:
(1)Canonical SMILES: C1CC(=O)N(C1=O)OC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24
(2)InChI: InChI=1S/C19H15NO5/c21-17-9-10-18(22)20(17)25-19(23)24-11-16-14-7-3-1-5-12(14)13-6-2-4-8-15(13)16/h1-8,16H,9-11H2
(3)InChIKey: WMSUFWLPZLCIHP-UHFFFAOYSA-N
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