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13139-17-8

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13139-17-8 Usage

Chemical Properties

white crystal powde

Uses

Different sources of media describe the Uses of 13139-17-8 differently. You can refer to the following data:
1. Reagents for the selective introduction of the Z-protecting group into amino compounds
2. N-(N-Benzyloxycarbonyloxy)succinimide is a reagent used in the preparation of peptide thioacids view peptide precursors. Also used in the preparation of amino glycoside derivatives for the function of topoisomerase for both human and bacterial inhibition.
3. N-(Benzyloxycarbonyloxy)succinimide (Cbz-OSu) is a common reagent for the carboxybenzyl protection of amines. This reaction is one of the key synthetic steps in the synthesis of:Enantiomers of cyclic methionine analogs viz, (R)-and (S)-3-aminotetrahydrothiophene- 3-carboxylic acid. 1′-H-Spiro-(indoline-3,4′-piperidine) and its derivatives.Total synthesis of (-)-diazonamide A. and (-)-sanglifehrin A. Cbz-OSu is widely employed to protect amino acid residues in peptide synthesis. It can also be used in N-trans diprotection of cyclen regioselectively.

Check Digit Verification of cas no

The CAS Registry Mumber 13139-17-8 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,3,1,3 and 9 respectively; the second part has 2 digits, 1 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 13139-17:
(7*1)+(6*3)+(5*1)+(4*3)+(3*9)+(2*1)+(1*7)=78
78 % 10 = 8
So 13139-17-8 is a valid CAS Registry Number.
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

13139-17-8 Well-known Company Product Price

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  • TCI America

  • (C1124)  N-Carbobenzoxyoxysuccinimide  >98.0%(N)

  • 13139-17-8

  • 25g

  • 195.00CNY

  • Detail
  • TCI America

  • (C1124)  N-Carbobenzoxyoxysuccinimide  >98.0%(N)

  • 13139-17-8

  • 250g

  • 990.00CNY

  • Detail
  • Alfa Aesar

  • (A12153)  N-(Benzyloxycarbonyloxy)succinimide, 98%   

  • 13139-17-8

  • 5g

  • 135.0CNY

  • Detail
  • Alfa Aesar

  • (A12153)  N-(Benzyloxycarbonyloxy)succinimide, 98%   

  • 13139-17-8

  • 25g

  • 312.0CNY

  • Detail
  • Alfa Aesar

  • (A12153)  N-(Benzyloxycarbonyloxy)succinimide, 98%   

  • 13139-17-8

  • 100g

  • 734.0CNY

  • Detail
  • Aldrich

  • (227781)  N-(Benzyloxycarbonyloxy)succinimide  98%

  • 13139-17-8

  • 227781-25G

  • 651.69CNY

  • Detail
  • Aldrich

  • (227781)  N-(Benzyloxycarbonyloxy)succinimide  98%

  • 13139-17-8

  • 227781-100G

  • 1,987.83CNY

  • Detail
  • Aldrich

  • (227781)  N-(Benzyloxycarbonyloxy)succinimide  98%

  • 13139-17-8

  • 227781-250G

  • 2,688.66CNY

  • Detail

13139-17-8SDS

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-(Benzyloxycarbonyloxy)succinimide

1.2 Other means of identification

Product number -
Other names N-Carbobenzoxyoxysuccinimide

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:13139-17-8 SDS

13139-17-8Synthetic route

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

1-hydroxy-pyrrolidine-2,5-dione

benzyl chloroformate
501-53-1

benzyl chloroformate

N-(Benzyloxycarbonyloxy)succinimide
13139-17-8

N-(Benzyloxycarbonyloxy)succinimide

Conditions
ConditionsYield
With sodium hydrogencarbonate In water; ethyl acetate at 15℃; for 19h; Large scale;90.5%
With TEA In 1,2-dimethoxyethane25%
With triethylamine In acetonitrile at 5℃; for 1h;
dicyclohexylamine salt of N-hydroxysuccinimide
82911-72-6

dicyclohexylamine salt of N-hydroxysuccinimide

benzyl chloroformate
501-53-1

benzyl chloroformate

N-(Benzyloxycarbonyloxy)succinimide
13139-17-8

N-(Benzyloxycarbonyloxy)succinimide

Conditions
ConditionsYield
In chloroform90%
succinic acid anhydride
108-30-5

succinic acid anhydride

benzyl chloroformate
501-53-1

benzyl chloroformate

N-(Benzyloxycarbonyloxy)succinimide
13139-17-8

N-(Benzyloxycarbonyloxy)succinimide

Conditions
ConditionsYield
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
74124-79-1

di(succinimido) carbonate

benzyl alcohol
100-51-6

benzyl alcohol

N-(Benzyloxycarbonyloxy)succinimide
13139-17-8

N-(Benzyloxycarbonyloxy)succinimide

Conditions
ConditionsYield
With triethylamine In acetonitrile at 20℃; Substitution;
With triethylamine In acetonitrile at 20℃; for 0.75 - 1h; Product distribution / selectivity;
N-cyclohexyl-cyclohexanamine
101-83-7

N-cyclohexyl-cyclohexanamine

chromium oxide activated nickel catalyst

chromium oxide activated nickel catalyst

N-(Benzyloxycarbonyloxy)succinimide
13139-17-8

N-(Benzyloxycarbonyloxy)succinimide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 95 percent / acetone
2: 90 percent / CHCl3
View Scheme
N-(Benzyloxycarbonyloxy)succinimide
13139-17-8

N-(Benzyloxycarbonyloxy)succinimide

5-Carbamimidoyl-1H-indole-2-carboxylic acid ethyl ester
199609-28-4

5-Carbamimidoyl-1H-indole-2-carboxylic acid ethyl ester

5-(Benzyloxycarbonylamino-imino-methyl)-1H-indole-2-carboxylic acid ethyl ester
199609-35-3

5-(Benzyloxycarbonylamino-imino-methyl)-1H-indole-2-carboxylic acid ethyl ester

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide Ambient temperature;100%
N-(Benzyloxycarbonyloxy)succinimide
13139-17-8

N-(Benzyloxycarbonyloxy)succinimide

ethanolamine
141-43-5

ethanolamine

benzyl 2-hydroxyethylcarbamate
77987-49-6

benzyl 2-hydroxyethylcarbamate

Conditions
ConditionsYield
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
13139-17-8

N-(Benzyloxycarbonyloxy)succinimide

5-hydroxypentylamine
2508-29-4

5-hydroxypentylamine

5-<(benzyloxycarbonyl)amino>pentanol
87905-98-4

5-<(benzyloxycarbonyl)amino>pentanol

Conditions
ConditionsYield
With sodium hydroxide In water; acetone at 20℃; for 4h;100%
In tetrahydrofuran at 20℃; for 19h; Acylation;
N-(Benzyloxycarbonyloxy)succinimide
13139-17-8

N-(Benzyloxycarbonyloxy)succinimide

(2S)-2-(2-methoxyethyl)piperidine
103639-57-2

(2S)-2-(2-methoxyethyl)piperidine

benzyl (2S)-2-(2-hydroxyethyl)piperidine-1-carboxylate
190967-63-6

benzyl (2S)-2-(2-hydroxyethyl)piperidine-1-carboxylate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 23℃; for 18h;100%
N-(Benzyloxycarbonyloxy)succinimide
13139-17-8

N-(Benzyloxycarbonyloxy)succinimide

4-Aminobutanol
13325-10-5

4-Aminobutanol

benzyl 4-hydroxybutylcarbamate
17996-13-3

benzyl 4-hydroxybutylcarbamate

Conditions
ConditionsYield
With sodium hydrogencarbonate In water; acetone at 20℃; for 4h;100%
With triethylamine In acetone at 20℃; for 7h;92.8%
N-(Benzyloxycarbonyloxy)succinimide
13139-17-8

N-(Benzyloxycarbonyloxy)succinimide

D-allylglycine
54594-06-8

D-allylglycine

(R)-2-(benzyloxycarbonylamino)pent-4-enoic acid
127474-54-8

(R)-2-(benzyloxycarbonylamino)pent-4-enoic acid

Conditions
ConditionsYield
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
13139-17-8

N-(Benzyloxycarbonyloxy)succinimide

L-allylglycine
16338-48-0

L-allylglycine

(S)-2-(benzyloxycarbonylamino)pent-4-enoic acid
78553-51-2

(S)-2-(benzyloxycarbonylamino)pent-4-enoic acid

Conditions
ConditionsYield
With water; triethylamine In 1,4-dioxane100%
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℃;
6-amino-2-hydroxymethyl-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester

6-amino-2-hydroxymethyl-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester

N-(Benzyloxycarbonyloxy)succinimide
13139-17-8

N-(Benzyloxycarbonyloxy)succinimide

(2R,1'S,3S,4S)-Nα-Boc-3,4-(Z-aminomethano)prolinol
916763-94-5

(2R,1'S,3S,4S)-Nα-Boc-3,4-(Z-aminomethano)prolinol

Conditions
ConditionsYield
With sodium hydrogencarbonate In water; acetone for 3h;100%
4-[(3-amino-2-hydroxypropyl)oxy]benzonitrile
227940-77-4

4-[(3-amino-2-hydroxypropyl)oxy]benzonitrile

N-(Benzyloxycarbonyloxy)succinimide
13139-17-8

N-(Benzyloxycarbonyloxy)succinimide

benzyl 3-(4-cyanophenoxy)-2-hydroxypropylcarbamate

benzyl 3-(4-cyanophenoxy)-2-hydroxypropylcarbamate

Conditions
ConditionsYield
With triethylamine In chloroform at 0 - 20℃;100%
N-(Benzyloxycarbonyloxy)succinimide
13139-17-8

N-(Benzyloxycarbonyloxy)succinimide

L-tert-Leucine
20859-02-3

L-tert-Leucine

(S)-N-carbobenzoxy-tert-butylleucine
62965-10-0

(S)-N-carbobenzoxy-tert-butylleucine

Conditions
ConditionsYield
With triethylamine In methanol at 20℃; for 14h;100%
1,2,3,6-tetrahydropyridine
694-05-3

1,2,3,6-tetrahydropyridine

N-(Benzyloxycarbonyloxy)succinimide
13139-17-8

N-(Benzyloxycarbonyloxy)succinimide

1-benzyloxycarbonyl-1,2,3,6-tetrahydropyridine
66207-23-6

1-benzyloxycarbonyl-1,2,3,6-tetrahydropyridine

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃;100%
With triethylamine In dichloromethane at 20 - 30℃; for 16h;
N-(Benzyloxycarbonyloxy)succinimide
13139-17-8

N-(Benzyloxycarbonyloxy)succinimide

tert-butyl 3-(aminomethyl)-4-hydroxypyrrolidine-1-carboxylate
773826-73-6

tert-butyl 3-(aminomethyl)-4-hydroxypyrrolidine-1-carboxylate

1,1-dimethylethyl 3-hydroxy-4-[({[(phenylmethyl)oxy]carbonyl}amino)methyl]-1-pyrrolidinecarboxylate
872716-50-2

1,1-dimethylethyl 3-hydroxy-4-[({[(phenylmethyl)oxy]carbonyl}amino)methyl]-1-pyrrolidinecarboxylate

Conditions
ConditionsYield
In dichloromethane at 0℃; for 1h;100%
N-(Benzyloxycarbonyloxy)succinimide
13139-17-8

N-(Benzyloxycarbonyloxy)succinimide

3-methyl-piperazine-1-carboxylic acid tert-butyl ester
120737-59-9

3-methyl-piperazine-1-carboxylic acid tert-butyl ester

O-benzyl carbamate
621-84-1

O-benzyl carbamate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane; water100%
N-(Benzyloxycarbonyloxy)succinimide
13139-17-8

N-(Benzyloxycarbonyloxy)succinimide

diisopropylethylamine (DIPEA)

diisopropylethylamine (DIPEA)

(S)-methyl pipecolinate hydrochloride
18650-39-0

(S)-methyl pipecolinate hydrochloride

(S)-1-(Benzyloxycarbonyl)-2-piperidine-carboxylic Acid Methyl Ester
60369-19-9, 60343-61-5

(S)-1-(Benzyloxycarbonyl)-2-piperidine-carboxylic Acid Methyl Ester

Conditions
ConditionsYield
In dichloromethane (DCM); hexane; ethyl acetate100%
N-(Benzyloxycarbonyloxy)succinimide
13139-17-8

N-(Benzyloxycarbonyloxy)succinimide

2-amino-2-methylpropanesulfonic acid sodium salt
60155-08-0

2-amino-2-methylpropanesulfonic acid sodium salt

sodium 2-(benzyloxycarbonylamino)-2-methylpropane-1-sulfonate
1037833-06-9

sodium 2-(benzyloxycarbonylamino)-2-methylpropane-1-sulfonate

Conditions
ConditionsYield
In tetrahydrofuran; water at 20℃; for 16h;100%
N-(Benzyloxycarbonyloxy)succinimide
13139-17-8

N-(Benzyloxycarbonyloxy)succinimide

3',4'-dideoxy-2-hydroxyneamine dicarbonate

3',4'-dideoxy-2-hydroxyneamine dicarbonate

1,3,2',6'-tetra-N-benzyloxycarbonyl-3',4'-dideoxy-2-hydroxyneamine
959918-76-4

1,3,2',6'-tetra-N-benzyloxycarbonyl-3',4'-dideoxy-2-hydroxyneamine

Conditions
ConditionsYield
With triethylamine In 1,2-dimethoxyethane; water at 45℃; Product distribution / selectivity;100%
N-(Benzyloxycarbonyloxy)succinimide
13139-17-8

N-(Benzyloxycarbonyloxy)succinimide

1,4,7,10-tetraazacyclododecan
294-90-6

1,4,7,10-tetraazacyclododecan

1,4,7,10-tetraaza-cyclododecane-1,7-dicarboxylic acid dibenzyl ester
162148-45-0

1,4,7,10-tetraaza-cyclododecane-1,7-dicarboxylic acid dibenzyl ester

Conditions
ConditionsYield
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
13139-17-8

N-(Benzyloxycarbonyloxy)succinimide

tert-butyl (3R,4R)-N-tert-butyloxycarbonyl-4-aminopyrrolidine-3-carboxylate
797038-63-2

tert-butyl (3R,4R)-N-tert-butyloxycarbonyl-4-aminopyrrolidine-3-carboxylate

(3R,4R)-di-tert-butyl 4-(benzyloxycarbonylamino)pyrrolidine-1,3-dicarboxylate
1033881-73-0

(3R,4R)-di-tert-butyl 4-(benzyloxycarbonylamino)pyrrolidine-1,3-dicarboxylate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 3h;100%
N-(Benzyloxycarbonyloxy)succinimide
13139-17-8

N-(Benzyloxycarbonyloxy)succinimide

D-phenylalanine ester
756458-80-7

D-phenylalanine ester

JM 3459-130

JM 3459-130

Conditions
ConditionsYield
With 4-methyl-morpholine In dichloromethane at 0 - 20℃;100%
N-(Benzyloxycarbonyloxy)succinimide
13139-17-8

N-(Benzyloxycarbonyloxy)succinimide

3,3'-Diamino-N-methyldipropylamine
105-83-9

3,3'-Diamino-N-methyldipropylamine

C23H31N3O4
1307864-23-8

C23H31N3O4

Conditions
ConditionsYield
In chloroform at 20℃; for 16h;100%
In chloroform at 20℃; for 16h;
In chloroform at 20℃; for 16h;
N-(Benzyloxycarbonyloxy)succinimide
13139-17-8

N-(Benzyloxycarbonyloxy)succinimide

N,N-dimethylethylenediamine
108-00-9

N,N-dimethylethylenediamine

(2-dimethylamino-ethyl)-carbamic acid benzyl ester

(2-dimethylamino-ethyl)-carbamic acid benzyl ester

Conditions
ConditionsYield
In chloroform at 0 - 20℃; for 2h; Inert atmosphere;100%
In chloroform at 0 - 20℃; for 2h; Inert atmosphere;
N-(Benzyloxycarbonyloxy)succinimide
13139-17-8

N-(Benzyloxycarbonyloxy)succinimide

C30H51N3O5
1376616-31-7

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
1236549-06-6

(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
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 1h;100%
N-(Benzyloxycarbonyloxy)succinimide
13139-17-8

N-(Benzyloxycarbonyloxy)succinimide

1-tert-butyl 2-methyl (2S,4S)-4-(aminomethyl)pyrrolidine-1,2-dicarboxylate

1-tert-butyl 2-methyl (2S,4S)-4-(aminomethyl)pyrrolidine-1,2-dicarboxylate

1-tert-butyl 2-methyl (2S,4S)-4-({[(benzyloxy)carbonyl]amino}methyl)pyrrolidine-1,2-dicarboxylate

1-tert-butyl 2-methyl (2S,4S)-4-({[(benzyloxy)carbonyl]amino}methyl)pyrrolidine-1,2-dicarboxylate

Conditions
ConditionsYield
In dichloromethane for 48h;100%
N-(Benzyloxycarbonyloxy)succinimide
13139-17-8

N-(Benzyloxycarbonyloxy)succinimide

Citrulline
372-75-8

Citrulline

Nα-benzyloxy-carbonyl-L-citrulline
6692-89-3

Nα-benzyloxy-carbonyl-L-citrulline

Conditions
ConditionsYield
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
13139-17-8

N-(Benzyloxycarbonyloxy)succinimide

β-D-galactopyranosyl-(1→4)-2-(t-butyloxycarbonylamino)-2-deoxy-β-D-glucopyranosyl-(1→3)-β-D-galactopyranosyl-(1→4)-2-deoxy-2-trifluoroacetamido-D-glucopyranoside-(1→3)-β-D-galactopyranosyl-(1→4)-2-amino-2-deoxy-α,β-D-glucopyranoside

β-D-galactopyranosyl-(1→4)-2-(t-butyloxycarbonylamino)-2-deoxy-β-D-glucopyranosyl-(1→3)-β-D-galactopyranosyl-(1→4)-2-deoxy-2-trifluoroacetamido-D-glucopyranoside-(1→3)-β-D-galactopyranosyl-(1→4)-2-amino-2-deoxy-α,β-D-glucopyranoside

β-D-galactopyranosyl-(1→4)-2-deoxy-2-(t-butyloxycarbonylamino)-β-D-glucopyranosyl-(1→3)-β-D-galactopyranosyl-(1→4)-2-deoxy-2-trifluoroacetamido-D-glucopyranoside-(1→3)-β-D-galactopyranosyl-(1→4)-2-(benzyloxycarbonylamino)-2-deoxy-α,β-D-glucopyranoside

β-D-galactopyranosyl-(1→4)-2-deoxy-2-(t-butyloxycarbonylamino)-β-D-glucopyranosyl-(1→3)-β-D-galactopyranosyl-(1→4)-2-deoxy-2-trifluoroacetamido-D-glucopyranoside-(1→3)-β-D-galactopyranosyl-(1→4)-2-(benzyloxycarbonylamino)-2-deoxy-α,β-D-glucopyranoside

Conditions
ConditionsYield
With sodium hydrogencarbonate In water at 37℃; for 1h; Inert atmosphere;100%
N-(Benzyloxycarbonyloxy)succinimide
13139-17-8

N-(Benzyloxycarbonyloxy)succinimide

(2S)-2-amino-3-(2-nitrophenyl)propanoic acid
1991-82-8, 35378-63-3, 19883-75-1

(2S)-2-amino-3-(2-nitrophenyl)propanoic acid

(S)-2-(((benzyloxy)carbonyl)amino)-3-(2-nitrophenyl)propanoic acid

(S)-2-(((benzyloxy)carbonyl)amino)-3-(2-nitrophenyl)propanoic acid

Conditions
ConditionsYield
With sodium hydrogencarbonate In water; acetonitrile at 20℃;100%
N-(Benzyloxycarbonyloxy)succinimide
13139-17-8

N-(Benzyloxycarbonyloxy)succinimide

4-nitro-3-phenyl-L-alanine
949-99-5

4-nitro-3-phenyl-L-alanine

(S)-2-(((benzyloxy)carbonyl)amino)-3-(4-nitrophenyl)propanoic acid
17224-90-7

(S)-2-(((benzyloxy)carbonyl)amino)-3-(4-nitrophenyl)propanoic acid

Conditions
ConditionsYield
With sodium hydrogencarbonate In water; acetonitrile at 20℃;100%
N-(Benzyloxycarbonyloxy)succinimide
13139-17-8

N-(Benzyloxycarbonyloxy)succinimide

(2S)-2-amino-3-(3-nitrophenyl)propanoic acid
19883-74-0

(2S)-2-amino-3-(3-nitrophenyl)propanoic acid

(S)-2-(((benzyloxy)carbonyl)amino)-3-(3-nitrophenyl)propanoic acid

(S)-2-(((benzyloxy)carbonyl)amino)-3-(3-nitrophenyl)propanoic acid

Conditions
ConditionsYield
With sodium hydrogencarbonate In water; acetonitrile at 20℃;100%
N-(Benzyloxycarbonyloxy)succinimide
13139-17-8

N-(Benzyloxycarbonyloxy)succinimide

C14H17NO2

C14H17NO2

C22H23NO4

C22H23NO4

Conditions
ConditionsYield
With sodium hydrogencarbonate at 20℃;100%
With sodium hydrogencarbonate at 20℃;100%
With sodium hydrogencarbonate at 20℃;100%
N-(Benzyloxycarbonyloxy)succinimide
13139-17-8

N-(Benzyloxycarbonyloxy)succinimide

rac-((RS)-1-amino-3-phenylpropyl)phosphinic acid

rac-((RS)-1-amino-3-phenylpropyl)phosphinic acid

(1-(((benzyloxy)carbonyl)amino)-3-phenylpropyl)phosphinic acid
234452-57-4

(1-(((benzyloxy)carbonyl)amino)-3-phenylpropyl)phosphinic acid

Conditions
ConditionsYield
With sodium carbonate In tetrahydrofuran; water at 0 - 20℃; for 24.25h; Inert atmosphere;100%

13139-17-8Relevant articles and documents

A large scale synthesis of mono- and di-urethane derivatives of lysine

Wiejak, Stanislaw,Masiukiewicz, Elzbieta,Rzeszotarska, Barbara

, p. 1489 - 1490 (1999)

In the search for a practical route to lysine diurethane derivatives useful for peptide synthesis, we elaborated the synthesis of N(ε)-tert- butoxycarbonyl-L-lysine copper(II) complex (1). This served as substrate for obtaining N(ε)-tert-butoxycarbonyl-L-lysine (2), N(α)-benzyloxycarbonyl- N(ε)-tert-butoxycarbonyl-L-lysine dicyclohexylamine salt (3) and N(α)-(9- fluorenyl)methoxycarbonyl-N(ε)-tert-butoxycarbonyl-L-lysine (4).

A Universal Labeling Strategy for Nucleic Acids in Expansion Microscopy

Hofkens, Johan,Leen, Volker,Rohand, Taoufik,Vandereyken, Katy,Vanheusden, Marisa,Voet, Thierry,Wen, Gang

supporting information, p. 13782 - 13789 (2021/09/11)

Expansion microscopy (ExM) enables the nanoscale imaging of ribonucleic acids (RNAs) on a conventional fluorescence microscope, providing information on the intricate patterns of gene expression at (sub)cellular resolution and within spatial context. To extend the use of such strategies, we examined a series of multivalent reagents that allow the labeling and grafting of deoxyribonucleic acid (DNA) oligonucleotide probes in a unified approach. We show that the reagents are directly compatible with third-generation in situ hybridization chain reaction RNA FISH (fluorescence in situ hybridization) techniques while displaying complete retention of the targeted transcripts. Furthermore, we validate and demonstrate that our labeling method is compatible with multicolor staining. Through oligonucleotide-conjugated antibodies, we demonstrate excellent performance in ×4 ExM and ×10 ExM, achieving a resolution of ~50 nm in ×10 ExM for both pre- and postexpansion labeling strategies. Our results indicate that our multivalent molecules enable the rapid functionalization of DNA oligonucleotides for ExM.

Synthesis method of N-(benzyloxycarbonyloxy)succinimide

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Paragraph 0005; 0008; 0010-0012; 0013; 0014; 0016; 0017, (2020/05/05)

The invention relates to a synthesis method of N-(benzyloxycarbonyloxy)succinimide; the invention mainly solves the technical problems of high raw material cost, overhigh reaction rate, severe heat release, high possibility of generating impurities, high product loss during refining and the like in an existing synthesis method. The synthesis method comprises the following steps: dissociating hydroxylamine hydrochloride in an aqueous solution by using NaOH, and carrying out a reaction with succinic anhydride to generate HOSu; carrying out a reaction of HOSu with Cbz-Cl in a mixed solution of water and ethyl acetate to generate a target compound Cbz-OSu. Cbz-OSu is commonly used as a polypeptide commonly used reagent, and a Z-amino protection reagent is selectively introduced in synthesis ofamino acids and aminoglycoside antibiotics.

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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