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82911-69-1 Usage

Chemical Properties

White powder

Uses

Different sources of media describe the Uses of 82911-69-1 differently. You can refer to the following data:
1. N-(9-Fluorenylmethoxycarbonyloxy)succinimide is used in conjunction with Isothiocyanate to conduct partial Edman Degradation on biologically active peptides.
2. N-protecting reagent for oligonucleotide and peptide syntheses
3. Reagent for the preparation of pure Fmoc amino acids free from contamination by Fmoc-dipeptides.

Purification Methods

Recrystallise the carbonate from CHCl3/Et2O, or from pet ether (b 40-60o). [Pauet Can J Chem 60 976 1982, Lapatsaris et al. Synthesis 671 1983.]

Check Digit Verification of cas no

The CAS Registry Mumber 82911-69-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 8,2,9,1 and 1 respectively; the second part has 2 digits, 6 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 82911-69:
(7*8)+(6*2)+(5*9)+(4*1)+(3*1)+(2*6)+(1*9)=141
141 % 10 = 1
So 82911-69-1 is a valid CAS Registry Number.
InChI:InChI=1/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

82911-69-1 Well-known Company Product Price

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  • (Code)Product description
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  • TCI America

  • (F0239)  N-[(9H-Fluoren-9-ylmethoxy)carbonyloxy]succinimide  >98.0%(HPLC)(T)

  • 82911-69-1

  • 5g

  • 90.00CNY

  • Detail
  • TCI America

  • (F0239)  N-[(9H-Fluoren-9-ylmethoxy)carbonyloxy]succinimide  >98.0%(HPLC)(T)

  • 82911-69-1

  • 25g

  • 195.00CNY

  • Detail
  • Alfa Aesar

  • (A13143)  N-(9-Fluorenylmethoxycarbonyloxy)succinimide, 98%   

  • 82911-69-1

  • 1g

  • 233.0CNY

  • Detail
  • Alfa Aesar

  • (A13143)  N-(9-Fluorenylmethoxycarbonyloxy)succinimide, 98%   

  • 82911-69-1

  • 5g

  • 701.0CNY

  • Detail
  • Alfa Aesar

  • (A13143)  N-(9-Fluorenylmethoxycarbonyloxy)succinimide, 98%   

  • 82911-69-1

  • 25g

  • 2976.0CNY

  • Detail
  • Aldrich

  • (46920)  FmocN-hydroxysuccinimideester  ≥98.0% (HPLC)

  • 82911-69-1

  • 46920-5G-F

  • 726.57CNY

  • Detail
  • Aldrich

  • (46920)  FmocN-hydroxysuccinimideester  ≥98.0% (HPLC)

  • 82911-69-1

  • 46920-25G-F

  • 2,937.87CNY

  • Detail
  • Aldrich

  • (46920)  FmocN-hydroxysuccinimideester  ≥98.0% (HPLC)

  • 82911-69-1

  • 46920-100G-F

  • 10,372.05CNY

  • Detail

82911-69-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name N-(9-Fluorenylmethoxycarbonyloxy)succinimide

1.2 Other means of identification

Product number -
Other names (2,5-dioxopyrrolidin-1-yl) 9H-fluoren-9-ylmethyl carbonate

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:82911-69-1 SDS

82911-69-1Synthetic route

1-hydroxy-pyrrolidine-2,5-dione
6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

(fluorenylmethoxy)carbonyl chloride
28920-43-6

(fluorenylmethoxy)carbonyl chloride

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
82911-69-1

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

Conditions
ConditionsYield
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
28920-43-6

(fluorenylmethoxy)carbonyl chloride

dicyclohexylamine salt of N-hydroxysuccinimide
82911-72-6

dicyclohexylamine salt of N-hydroxysuccinimide

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
82911-69-1

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

Conditions
ConditionsYield
In chloroform90%
C16H26N2O3

C16H26N2O3

(fluorenylmethoxy)carbonyl chloride
28920-43-6

(fluorenylmethoxy)carbonyl chloride

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
82911-69-1

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

Conditions
ConditionsYield
In chloroform90%
2,5-dioxopyrrolidin-1-yl carbonochloridate
15149-73-2

2,5-dioxopyrrolidin-1-yl carbonochloridate

9-Fluorenylmethanol
24324-17-2

9-Fluorenylmethanol

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
82911-69-1

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

Conditions
ConditionsYield
With pyridine In dichloromethane for 5h; Ambient temperature;72%
N-cyclohexyl-cyclohexanamine
101-83-7

N-cyclohexyl-cyclohexanamine

chromium oxide activated nickel catalyst

chromium oxide activated nickel catalyst

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
82911-69-1

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 95 percent / acetone
2: 90 percent / CHCl3
View Scheme
L-serin
56-45-1

L-serin

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
82911-69-1

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

N-(9H-fluoren-9-ylmethoxycarbonyl)-L-serine
73724-45-5

N-(9H-fluoren-9-ylmethoxycarbonyl)-L-serine

Conditions
ConditionsYield
With sodium hydrogencarbonate100%
With sodium carbonate In 1,4-dioxane97%
With sodium hydrogencarbonate In water; acetonitrile94%
L-threonine
72-19-5

L-threonine

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
82911-69-1

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

Fmoc-Thr-OH
73731-37-0

Fmoc-Thr-OH

Conditions
ConditionsYield
With sodium hydrogencarbonate100%
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 acetone97%
methyl (2S)-2-amino-3-hydroxypropanoate hydrochloride
5680-80-8

methyl (2S)-2-amino-3-hydroxypropanoate hydrochloride

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
82911-69-1

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

N-[(9-fluorenylmethoxy)carbonyl]-L-serine methyl ester
82911-78-2

N-[(9-fluorenylmethoxy)carbonyl]-L-serine methyl ester

Conditions
ConditionsYield
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
82911-69-1

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

3-(3-(amino-4-methoxyphenylmethyl)-4-methoxyphenyl)propionic acid
117286-86-9

3-(3-(amino-4-methoxyphenylmethyl)-4-methoxyphenyl)propionic acid

3-(α-fluoren-9-ylmethoxycarbonylamino-4-methoxybenzyl)-4-methoxyphenylpropionic acid
117286-85-8

3-(α-fluoren-9-ylmethoxycarbonylamino-4-methoxybenzyl)-4-methoxyphenylpropionic acid

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide for 1h; Ambient temperature;100%
N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
82911-69-1

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

AmBisome
1397-89-3

AmBisome

3′-N-Fmoc-AmB
127970-81-4

3′-N-Fmoc-AmB

Conditions
ConditionsYield
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
82911-69-1

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

(S)-2-Amino-4-(2,4,6-trimethoxy-benzylsulfamoyl)-butyric acid

(S)-2-Amino-4-(2,4,6-trimethoxy-benzylsulfamoyl)-butyric acid

(S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-4-(2,4,6-trimethoxy-benzylsulfamoyl)-butyric acid

(S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-4-(2,4,6-trimethoxy-benzylsulfamoyl)-butyric acid

Conditions
ConditionsYield
With sodium hydrogencarbonate In water; acetone for 12h; Ambient temperature;100%
N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
82911-69-1

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

(R)-2-Amino-3-(2-tert-butoxycarbonylamino-ethylsulfamoyl)-propionic acid
152871-80-2

(R)-2-Amino-3-(2-tert-butoxycarbonylamino-ethylsulfamoyl)-propionic acid

(R)-3-(2-tert-Butoxycarbonylamino-ethylsulfamoyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid

(R)-3-(2-tert-Butoxycarbonylamino-ethylsulfamoyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid

Conditions
ConditionsYield
With sodium hydrogencarbonate In water; acetone for 12h; Ambient temperature;100%
N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
82911-69-1

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

(R)-2-Amino-4-(2-tert-butoxycarbonylamino-ethylsulfamoyl)-butyric acid
152871-82-4

(R)-2-Amino-4-(2-tert-butoxycarbonylamino-ethylsulfamoyl)-butyric acid

(R)-4-(2-tert-Butoxycarbonylamino-ethylsulfamoyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid

(R)-4-(2-tert-Butoxycarbonylamino-ethylsulfamoyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid

Conditions
ConditionsYield
With sodium hydrogencarbonate In water; acetone for 12h; Ambient temperature;100%
N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
82911-69-1

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

Propargylamine
2450-71-7

Propargylamine

Fmoc-N-propargylamine
127896-08-6

Fmoc-N-propargylamine

Conditions
ConditionsYield
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)
16874-12-7

Tyr(tBu)

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
82911-69-1

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

(S)-tert-butyl 2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(4-hydroxyphenyl)propanoate
133852-23-0

(S)-tert-butyl 2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(4-hydroxyphenyl)propanoate

Conditions
ConditionsYield
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
82911-69-1

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

(2S)-1,2,3,6-tetrahydropyridine-2-carboxylic acid
31456-71-0

(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
207733-59-3

(S)-3,6-Dihydro-2H-pyridine-1,2-dicarboxylic acid 1-(9H-fluoren-9-ylmethyl) ester

Conditions
ConditionsYield
With sodium hydroxide; sodium hydrogencarbonate100%
N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
82911-69-1

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

(3S,6R,8aR)-6-Amino-5-oxo-octahydro-indolizine-3-carboxylic acid

(3S,6R,8aR)-6-Amino-5-oxo-octahydro-indolizine-3-carboxylic acid

(3R,6R,9S)-1-aza-9-carboxy-3-(9'-fluorenylmethoxycarbonylamino)-2-oxo-bicyclo[4.3.0]nonane
326490-44-2

(3R,6R,9S)-1-aza-9-carboxy-3-(9'-fluorenylmethoxycarbonylamino)-2-oxo-bicyclo[4.3.0]nonane

Conditions
ConditionsYield
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
82911-69-1

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

(3S,6S,8aR)-6-Amino-5-oxo-octahydro-indolizine-3-carboxylic acid

(3S,6S,8aR)-6-Amino-5-oxo-octahydro-indolizine-3-carboxylic acid

(2S,6R,9S)-2-oxo-3-(9-fluorenyloxycarbonylamino)-1-azabicyclo[4.2.0]nonane-9-carboxylic acid
326490-43-1

(2S,6R,9S)-2-oxo-3-(9-fluorenyloxycarbonylamino)-1-azabicyclo[4.2.0]nonane-9-carboxylic acid

Conditions
ConditionsYield
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
82911-69-1

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

(3S,6R,8aS)-6-Amino-5-oxo-octahydro-indolizine-3-carboxylic acid

(3S,6R,8aS)-6-Amino-5-oxo-octahydro-indolizine-3-carboxylic acid

(3R,6S,9S)-1-aza-9-carboxy-3-(9'-fluorenylmethoxycarbonylamino)-2-oxo-bicyclo[4.3.0]nonane
326490-42-0

(3R,6S,9S)-1-aza-9-carboxy-3-(9'-fluorenylmethoxycarbonylamino)-2-oxo-bicyclo[4.3.0]nonane

Conditions
ConditionsYield
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
82911-69-1

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

(3S,6S,8aS)-6-Amino-5-oxo-octahydro-indolizine-3-carboxylic acid
934660-55-6

(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
326490-41-9

(3S,6S,9S)-2-oxo-3-(N-(9-fluorenylmethoxycarbonyl)amino)-1-azabicyclo[4.3.0]nonane-9-carboxylic acid

Conditions
ConditionsYield
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; water265 mg
N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
82911-69-1

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

(3S,6R,9aR)-6-Amino-5-oxo-octahydro-pyrrolo[1,2-a]azepine-3-carboxylic acid

(3S,6R,9aR)-6-Amino-5-oxo-octahydro-pyrrolo[1,2-a]azepine-3-carboxylic acid

(3R,7R,10S)-1-aza-10-carboxy-3-(9'-fluorenylmethoxycarbonylamino)-2-oxo-bicyclo[5.3.0]decane
337513-07-2

(3R,7R,10S)-1-aza-10-carboxy-3-(9'-fluorenylmethoxycarbonylamino)-2-oxo-bicyclo[5.3.0]decane

Conditions
ConditionsYield
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
82911-69-1

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

(3S,6S,9aR)-6-Amino-5-oxo-octahydro-pyrrolo[1,2-a]azepine-3-carboxylic acid

(3S,6S,9aR)-6-Amino-5-oxo-octahydro-pyrrolo[1,2-a]azepine-3-carboxylic acid

(3S,7R,10S)-2-oxo-3-N-(9-fluorenylmethyloxycarbonyl)amino-1-azabicyclo[5.3.0]decane-10-carboxylic acid
270585-84-7

(3S,7R,10S)-2-oxo-3-N-(9-fluorenylmethyloxycarbonyl)amino-1-azabicyclo[5.3.0]decane-10-carboxylic acid

Conditions
ConditionsYield
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
82911-69-1

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

(3S,6R,9aS)-6-Amino-5-oxo-octahydro-pyrrolo[1,2-a]azepine-3-carboxylic acid

(3S,6R,9aS)-6-Amino-5-oxo-octahydro-pyrrolo[1,2-a]azepine-3-carboxylic acid

(3R,7S,10S)-1-aza-10-carboxy-3-(9'-fluorenylmethoxycarbonylamino)-2-oxo-bicyclo[5.3.0]decane
326490-45-3

(3R,7S,10S)-1-aza-10-carboxy-3-(9'-fluorenylmethoxycarbonylamino)-2-oxo-bicyclo[5.3.0]decane

Conditions
ConditionsYield
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
82911-69-1

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

(3S,6S,9aS)-6-Amino-5-oxo-octahydro-pyrrolo[1,2-a]azepine-3-carboxylic acid

(3S,6S,9aS)-6-Amino-5-oxo-octahydro-pyrrolo[1,2-a]azepine-3-carboxylic acid

(3S,7S,10S)-2-oxo-3-N-(9-fluorenylmethyloxycarbonyl)amino-1-azabicyclo[5.3.0]decane-10-carboxylic acid
220719-79-9

(3S,7S,10S)-2-oxo-3-N-(9-fluorenylmethyloxycarbonyl)amino-1-azabicyclo[5.3.0]decane-10-carboxylic acid

Conditions
ConditionsYield
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
82911-69-1

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

(2S,3S)-2-amino-3-(1-(tert-butoxycarbonyl)-1H-indol-3-yl)butanoic acid

(2S,3S)-2-amino-3-(1-(tert-butoxycarbonyl)-1H-indol-3-yl)butanoic acid

(2S,3S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(1-(tert-butoxycarbonyl)-1H-indol-3-yl)butanoic acid

(2S,3S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(1-(tert-butoxycarbonyl)-1H-indol-3-yl)butanoic acid

Conditions
ConditionsYield
With triethylamine In methanol100%
(S)-2-amino-2-cyclopentylacetic acid
2521-84-8

(S)-2-amino-2-cyclopentylacetic acid

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
82911-69-1

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

(S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-cyclopentylacetic acid

(S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-cyclopentylacetic acid

Conditions
ConditionsYield
With sodium carbonate In 1,4-dioxane; water100%
glycinamide hydrochloride
1668-10-6

glycinamide hydrochloride

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
82911-69-1

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

Fmoc-Gly-NH2
115057-37-9

Fmoc-Gly-NH2

Conditions
ConditionsYield
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
82911-69-1

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

N-α-tert-butyloxycarbonyl-(2S,4R)-2-tert-butyloxycarbonylmethyl-4-(adenin-9'-yl)-pyrrolidine
714230-15-6

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
714230-17-8

N-α-9-fluorenylmethoxycarbonyl-(2S,4R)-2-hydroxycarbonylmethoxymethyl-4-(adenin-9'-yl)-pyrrolidine

Conditions
ConditionsYield
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%
3-amino-3-deoxy-1,2-O-isopropylidene-α-L-ribofuranose

3-amino-3-deoxy-1,2-O-isopropylidene-α-L-ribofuranose

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
82911-69-1

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

3-deoxy-3-(9-fluorenylmethoxycarbonyl)amino-1,2-O-isopropylidene-α-L-ribofuranose
928306-69-8

3-deoxy-3-(9-fluorenylmethoxycarbonyl)amino-1,2-O-isopropylidene-α-L-ribofuranose

Conditions
ConditionsYield
With sodium hydrogencarbonate In water; acetone at 20℃; for 1h;100%
(2S,4S)-4-diphenylphosphinothioyl-proline hydrochloride

(2S,4S)-4-diphenylphosphinothioyl-proline hydrochloride

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
82911-69-1

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

(2S,4S)-N-fluorenylmethoxycarbonyl-2-carboxy-4-diphenylphosphinothioyl-pyrrolidine
178158-98-0

(2S,4S)-N-fluorenylmethoxycarbonyl-2-carboxy-4-diphenylphosphinothioyl-pyrrolidine

Conditions
ConditionsYield
With sodium hydrogencarbonate In water; acetone100%
4-Aminobutanol
13325-10-5

4-Aminobutanol

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
82911-69-1

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

(9H-fluoren-9-yl)methyl (4-hydroxybutyl)carbamate
209115-32-2

(9H-fluoren-9-yl)methyl (4-hydroxybutyl)carbamate

Conditions
ConditionsYield
With pyridine In methanol at 23℃; for 23h;100%
In tetrahydrofuran; water at 20℃; Cooling with ice;1.21 g
6-amino-1-hexanol
4048-33-3

6-amino-1-hexanol

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
82911-69-1

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

(9H-fluoren-9-yl)methyl (6-hydroxyhexyl)carbamate
127903-20-2

(9H-fluoren-9-yl)methyl (6-hydroxyhexyl)carbamate

Conditions
ConditionsYield
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
1-amino-2-butyl-cycloprop-2-ene carboxylic acid trifluoroacetic acid salt

1-amino-2-butyl-cycloprop-2-ene carboxylic acid trifluoroacetic acid salt

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
82911-69-1

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

2-butyl-1-(9H-fluoren-9-ylmethoxycarbonylamino)-cycloprop-2-ene carboxylic acid

2-butyl-1-(9H-fluoren-9-ylmethoxycarbonylamino)-cycloprop-2-ene carboxylic acid

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In water; acetonitrile at 20℃; for 4h;100%
2-((S)-1-{(S)-2-[(2S,3S)-2-((2S,3S)-2-{[(S)-1-((S)-2-Amino-3-phenyl-propionyl)-pyrrolidine-2-carbonyl]-amino}-3-methyl-pentanoylamino)-3-hydroxy-butyrylamino]-3-phenyl-propionyl}-pyrrolidin-2-yl)-thiazole-4-carboxylic acid ethyl ester; hydrochloride

2-((S)-1-{(S)-2-[(2S,3S)-2-((2S,3S)-2-{[(S)-1-((S)-2-Amino-3-phenyl-propionyl)-pyrrolidine-2-carbonyl]-amino}-3-methyl-pentanoylamino)-3-hydroxy-butyrylamino]-3-phenyl-propionyl}-pyrrolidin-2-yl)-thiazole-4-carboxylic acid ethyl ester; hydrochloride

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
82911-69-1

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

2-[1-(2-{2-[2-({1-[2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-phenyl-propionyl]-pyrrolidine-2-carbonyl}-amino)-3-methyl-pentanoylamino]-3-hydroxy-butyrylamino}-3-phenyl-propionyl)-pyrrolidin-2-yl]-thiazole-4-carboxylic acid ethyl ester

2-[1-(2-{2-[2-({1-[2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-phenyl-propionyl]-pyrrolidine-2-carbonyl}-amino)-3-methyl-pentanoylamino]-3-hydroxy-butyrylamino}-3-phenyl-propionyl)-pyrrolidin-2-yl]-thiazole-4-carboxylic acid ethyl ester

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane pH=9;100%
N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
82911-69-1

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

ethanolamine
141-43-5

ethanolamine

N-(9-fluorenylmethoxycarbonyl)-2-aminoethanol
105496-31-9

N-(9-fluorenylmethoxycarbonyl)-2-aminoethanol

Conditions
ConditionsYield
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%

82911-69-1Relevant articles and documents

Method for synthesizing 9-fluorenylmethylsuccinimido carbonate by one-pot two-phase method

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Paragraph 0011; 0024-0029, (2020/03/03)

The invention relates to the technical field of organic synthesis, specifically to a method for synthesizing 9-fluorenylmethylsuccinimido carbonate by a one-pot two-phase method. The method comprisesthe following steps: adding purified water and hydroxylamine sulfate into a reaction container, dropwise adding liquid caustic soda under stirring, after the liquid caustic soda is dropwise added, adding butanedioic anhydride in batches, and carrying out high-temperature vacuum dehydration under acid catalysis until no water is extracted out so as to prepare an N-hydroxysuccinimide solution; adding a chloroformic acid-9-fluorenyl methyl ester solution into the N-hydroxysuccinimide solution, and controlling a temperature at 0 to 60 DEG C; after the chloroformic acid-9-fluorenyl methyl ester solution is added, starting to dropwise add an aqueous alkali solution; after the aqueous alkali solution is dropwise added, separating out an organic layer, carrying out concentrating to dryness, and carrying out recrystallizing so as to obtain a 9-fluorenylmethylsuccinimido carbonate finished product. The above-mentioned method provided by the invention innovatively adopts the one-pot two-phase method; a reaction liquid containing N-hydroxysuccinimide is directly used for synthesizing the 9-fluorenylmethylsuccinimido carbonate in a two-phase reaction manner; process steps are effectively reduced; and the method is applicable to large-scale industrial production.

The two pathways for effective orthogonal protection of L-ornithine, for amino acylation of 5'-O-Pivaloyl nucleosides, describe the general and important role for the successful imitation, during the synthesis of the model substrates for the ribosomal mimic reaction

Bayryamov, Stanislav G.,Vassilev, Nikolay G.,Petkov, Dimiter D.

experimental part, p. 889 - 898 (2011/12/14)

Bz(NO2)-Orn(Boc)-OCH2CN was synthesized as an amino acid component with effective and successful orthogonal protection for amino acylation of 5'-O-Pivaloyl nucleosides and preparation of substrates for model ribosome reactions. The synthesis was carried out using suitable combinations of the methods of peptide synthesis and modification of amino acids.

Scalable synthesis of Nα-benzyloxycarbonyl-L-ornithine and of Nα-(9-fluorenylmethoxy)carbonyl-L-ornithine

Masiukiewicz, Elzbieta,Wiejak, Stanislaw,Rzeszotarska, Barbara

, p. 531 - 537 (2007/10/03)

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