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2188-18-3

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2188-18-3 Usage

Uses

Boc-L-Nitroarginine, can be used in peptide chemistry. It has been also shown to act as NO synthase inhibitor, and thus used in the study of The effects of methylene blue (MB) for treatment of sepsis induced by bowel perforation.

Check Digit Verification of cas no

The CAS Registry Mumber 2188-18-3 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,1,8 and 8 respectively; the second part has 2 digits, 1 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 2188-18:
(6*2)+(5*1)+(4*8)+(3*8)+(2*1)+(1*8)=83
83 % 10 = 3
So 2188-18-3 is a valid CAS Registry Number.
InChI:InChI=1/C11H21N5O6/c1-11(2,3)22-10(19)14-7(8(17)18)5-4-6-13-9(12)15-16(20)21/h7H,4-6H2,1-3H3,(H,14,19)(H,17,18)(H3,12,13,15)/t7-/m1/s1

2188-18-3 Well-known Company Product Price

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  • Alfa Aesar

  • (H62339)  Nalpha-Boc-Nomega-nitro-L-arginine, 98%   

  • 2188-18-3

  • 25g

  • 596.0CNY

  • Detail
  • Alfa Aesar

  • (H62339)  Nalpha-Boc-Nomega-nitro-L-arginine, 98%   

  • 2188-18-3

  • 100g

  • 2150.0CNY

  • Detail
  • Aldrich

  • (15470)  Boc-Arg(NO2)-OH  ≥98.5% (calc. based on dry substance, T)

  • 2188-18-3

  • 15470-25G

  • 1,122.03CNY

  • Detail

2188-18-3SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name (2S)-5-[[amino(nitramido)methylidene]amino]-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoic acid

1.2 Other means of identification

Product number -
Other names Boc-L-Nitroarginine

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:2188-18-3 SDS

2188-18-3Synthetic route

N-nitro-L-arginine
2149-70-4

N-nitro-L-arginine

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

Boc-Arg(NO2)-OH
2188-18-3

Boc-Arg(NO2)-OH

Conditions
ConditionsYield
With sodium hydroxide; magnesium oxide In 1,4-dioxane; water for 24h; Ambient temperature;95%
With sodium hydroxide In 1,4-dioxane; water at 20 - 40℃; for 15h; pH=8.5;82%
N-nitro-L-arginine
2149-70-4

N-nitro-L-arginine

tert-butyl 2-oxo-1,3-oxazole-3(2H)-carboxylate
75844-68-7

tert-butyl 2-oxo-1,3-oxazole-3(2H)-carboxylate

Boc-Arg(NO2)-OH
2188-18-3

Boc-Arg(NO2)-OH

Conditions
ConditionsYield
With dmap; triethylamine In 1,4-dioxane; water for 15h; Ambient temperature;82%
N-nitro-L-arginine
2149-70-4

N-nitro-L-arginine

dimethylsulfonium methylsulfate

dimethylsulfonium methylsulfate

Boc-Arg(NO2)-OH
2188-18-3

Boc-Arg(NO2)-OH

Conditions
ConditionsYield
With triethylamine In water Ambient temperature;78%
N-(tert-butyloxycarbonyl) azide
1070-19-5

N-(tert-butyloxycarbonyl) azide

N-nitro-L-arginine
2149-70-4

N-nitro-L-arginine

Boc-Arg(NO2)-OH
2188-18-3

Boc-Arg(NO2)-OH

Conditions
ConditionsYield
With sodium hydroxide In 1,4-dioxane
(i) Na2CO3, aq. dioxane, (ii) /BRN= 1363586/; Multistep reaction;
With magnesium oxide
With triethylamine In water; N,N-dimethyl-formamide
N-nitro-L-arginine
2149-70-4

N-nitro-L-arginine

2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile
58632-95-4

2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile

Boc-Arg(NO2)-OH
2188-18-3

Boc-Arg(NO2)-OH

Conditions
ConditionsYield
With triethylamine
t-butylpentachlorophenyl carbonate
18942-25-1

t-butylpentachlorophenyl carbonate

N-ω-nitro-L-arginine

N-ω-nitro-L-arginine

Boc-Arg(NO2)-OH
2188-18-3

Boc-Arg(NO2)-OH

Conditions
ConditionsYield
With triethylamine In chloroform; N,N-dimethyl-formamide
t-butyloxycarbonyl-L-arginine
13726-76-6

t-butyloxycarbonyl-L-arginine

Boc-Arg(NO2)-OH
2188-18-3

Boc-Arg(NO2)-OH

Conditions
ConditionsYield
With sulfuric acid; nitric acid Nitration;
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

Boc-Arg(NO2)-OH
2188-18-3

Boc-Arg(NO2)-OH

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 80 percent / Et3N / acetonitrile / 5 h / 5 °C
2: 78 percent / Et3N / H2O / Ambient temperature
View Scheme
Boc-Arg(NO2)-OH
2188-18-3

Boc-Arg(NO2)-OH

N1-benzyloxycarbonyl-N8-D-leucyl-1,8-octanediamine
175216-23-6

N1-benzyloxycarbonyl-N8-D-leucyl-1,8-octanediamine

N1-benzyloxycarbonyl-N8-(Nα-t-butoxycarbonyl-Ng-nitroarginyl-D-leucyl)-1,8-octanediamine
175216-24-7

N1-benzyloxycarbonyl-N8-(Nα-t-butoxycarbonyl-Ng-nitroarginyl-D-leucyl)-1,8-octanediamine

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0 - 20℃; Acylation;100%
Boc-Arg(NO2)-OH
2188-18-3

Boc-Arg(NO2)-OH

(3S)-3-amino-1-(tert-butoxycarbonyl)-pyrrolidine
147081-44-5

(3S)-3-amino-1-(tert-butoxycarbonyl)-pyrrolidine

(3S)-3-({(2S)-2-[(tert-butoxycarbonyl)amino]-5-(3-nitroguanidino)pentanoyl}amino)pyrrolidine-1-carboxylic acid tert-butyl ester

(3S)-3-({(2S)-2-[(tert-butoxycarbonyl)amino]-5-(3-nitroguanidino)pentanoyl}amino)pyrrolidine-1-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃;99%
Boc-Arg(NO2)-OH
2188-18-3

Boc-Arg(NO2)-OH

methyl L-isoleucinate hydrochloride
18598-74-8

methyl L-isoleucinate hydrochloride

A

1,3-Dicyclohexylurea
2387-23-7

1,3-Dicyclohexylurea

B

(tert-butoxycarbonyl)-NG-nitroarginylisoleucyl methyl ester
102342-09-6

(tert-butoxycarbonyl)-NG-nitroarginylisoleucyl methyl ester

Conditions
ConditionsYield
With benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide 1.) ice bath, 1 h, 2.) 23 deg C, 15 h;A n/a
B 95%
Boc-Arg(NO2)-OH
2188-18-3

Boc-Arg(NO2)-OH

benzyl chloride
100-44-7

benzyl chloride

benzyl Nα-Boc-Nω-nitro-L-argininate
94770-45-3

benzyl Nα-Boc-Nω-nitro-L-argininate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; sodium iodide In N,N-dimethyl-formamide at 80℃; for 7h;95%
Boc-Arg(NO2)-OH
2188-18-3

Boc-Arg(NO2)-OH

tert-butyl L-alaninate hydrochloride
13404-22-3

tert-butyl L-alaninate hydrochloride

Boc-Arg(NO2)-Ala-OBu-t
107540-28-3

Boc-Arg(NO2)-Ala-OBu-t

Conditions
ConditionsYield
With 4-methyl-morpholine; benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran 1.) -10 deg C, 1 h, 2.) room temp., 18 h;94%
Boc-Arg(NO2)-OH
2188-18-3

Boc-Arg(NO2)-OH

benzyl glycinate benzenesulfonate

benzyl glycinate benzenesulfonate

Nα-tert-butyloxycarbonyl-NG-nitroarginylglycine benzyl ester
83103-21-3

Nα-tert-butyloxycarbonyl-NG-nitroarginylglycine benzyl ester

Conditions
ConditionsYield
Stage #1: Boc-Arg(NO2)-OH With benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran at 0℃; for 0.333333h;
Stage #2: benzyl glycinate benzenesulfonate With 4-methyl-morpholine In tetrahydrofuran at 20℃; for 24h;
94%
tert-butyl (3R)3-aminopiperidine-1-carboxylate
188111-79-7

tert-butyl (3R)3-aminopiperidine-1-carboxylate

Boc-Arg(NO2)-OH
2188-18-3

Boc-Arg(NO2)-OH

(3R)-3-({(2S)-2-[(tert-butoxycarbonyl)amino]-5-(3-nitroguanidino)pentanoyl}amino)piperidine-1-carboxylic acid tert-butyl ester

(3R)-3-({(2S)-2-[(tert-butoxycarbonyl)amino]-5-(3-nitroguanidino)pentanoyl}amino)piperidine-1-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃;92%
2,3,4,5,6-pentafluorophenol
771-61-9

2,3,4,5,6-pentafluorophenol

Boc-Arg(NO2)-OH
2188-18-3

Boc-Arg(NO2)-OH

Nα-tert-butoxycarbonyl-Nω-nitro-L-arginine pentafluorophenyl ester
57866-90-7

Nα-tert-butoxycarbonyl-Nω-nitro-L-arginine pentafluorophenyl ester

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In dichloromethane; N,N-dimethyl-formamide at 0℃; for 12h;91%
Boc-Arg(NO2)-OH
2188-18-3

Boc-Arg(NO2)-OH

(R)-3-aminopyrrolidine-1-carboxylic acid tert-butyl ester
147081-49-0

(R)-3-aminopyrrolidine-1-carboxylic acid tert-butyl ester

(3R)-3-({(2S)-2-[(tert-butoxycarbonyl)amino]-5-(3-nitroguanidino)pentanoyl}amino)pyrrolidine-1-carboxylic acid tert-butyl ester

(3R)-3-({(2S)-2-[(tert-butoxycarbonyl)amino]-5-(3-nitroguanidino)pentanoyl}amino)pyrrolidine-1-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃;91%
Boc-Arg(NO2)-OH
2188-18-3

Boc-Arg(NO2)-OH

benzyl (2S)-2-pyrrolidinecarboxylate hydrochloride
16652-71-4

benzyl (2S)-2-pyrrolidinecarboxylate hydrochloride

Boc-Arg(NO2)-Pro-OBzl
54046-53-6

Boc-Arg(NO2)-Pro-OBzl

Conditions
ConditionsYield
Stage #1: Boc-Arg(NO2)-OH With 4-methyl-morpholine; isobutyl chloroformate In acetonitrile at -15℃; for 0.166667h;
Stage #2: With 1-hydroxybenzotriazol-hydrate In acetonitrile for 0.166667h; cooling;
Stage #3: benzyl (2S)-2-pyrrolidinecarboxylate hydrochloride With 4-methyl-morpholine In N,N-dimethyl-formamide; acetonitrile at 20℃; pH=8;
90.5%
Stage #1: Boc-Arg(NO2)-OH With 4-methyl-morpholine; isobutyl chloroformate In acetonitrile at -15 - 0℃; for 0.166667h;
Stage #2: With benzotriazol-1-ol In N,N-dimethyl-formamide; acetonitrile at -15℃; for 0.166667h;
Stage #3: benzyl (2S)-2-pyrrolidinecarboxylate hydrochloride In N,N-dimethyl-formamide; acetonitrile at -15 - 20℃; pH=8;
88%
Boc-Arg(NO2)-OH
2188-18-3

Boc-Arg(NO2)-OH

H-Arg(NO2)-Ala-OBu-t
107540-29-4

H-Arg(NO2)-Ala-OBu-t

Boc-2-Ala-OBu-t
107540-30-7

Boc-2-Ala-OBu-t

Conditions
ConditionsYield
With 4-methyl-morpholine; benzotriazol-1-ol; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide 1.) -10 deg C, 1 h, 2.) room temp., 18 h;90%
H-Gly-Asp(OBzl)-Val-OBzl*HCl

H-Gly-Asp(OBzl)-Val-OBzl*HCl

Boc-Arg(NO2)-OH
2188-18-3

Boc-Arg(NO2)-OH

Boc-Arg(Nω-NO2)-Gly-Asp(OBn)-Val-OBn
350688-05-0

Boc-Arg(Nω-NO2)-Gly-Asp(OBn)-Val-OBn

Conditions
ConditionsYield
Stage #1: Boc-Arg(NO2)-OH With 1-hydroxybenzotriazol-hydrate; dicyclohexyl-carbodiimide In tetrahydrofuran at 0℃; for 0.5h;
Stage #2: H-Gly-Asp(OBzl)-Val-OBzl*HCl With 4-methyl-morpholine In tetrahydrofuran at 20℃; for 8h; pH=8.5; Further stages.;
90%
Stage #1: Boc-Arg(NO2)-OH With benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran for 0.333333h; Cooling with ice;
Stage #2: H-Gly-Asp(OBzl)-Val-OBzl*HCl With 4-methyl-morpholine In tetrahydrofuran at 20℃; for 24h;
86%
Boc-Arg(NO2)-OH
2188-18-3

Boc-Arg(NO2)-OH

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
152460-10-1

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine

C27H34N10O5

C27H34N10O5

Conditions
ConditionsYield
With O‑(6‑chlorobezotriazol‑1‑yl)‑N,N,N,N‑tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 10 - 20℃; for 5h;90%
Boc-Arg(NO2)-OH
2188-18-3

Boc-Arg(NO2)-OH

H-Pro-Arg(NO2)-Pro-OBzl monohydrochloride

H-Pro-Arg(NO2)-Pro-OBzl monohydrochloride

Boc-Arg(NO2)-Pro-Arg(NO2)-Pro-OBzl
423775-43-3

Boc-Arg(NO2)-Pro-Arg(NO2)-Pro-OBzl

Conditions
ConditionsYield
With 4-methyl-morpholine; isobutyl chloroformate In acetonitrile89.2%
Stage #1: H-Pro-Arg(NO2)-Pro-OBzl monohydrochloride With 4-methyl-morpholine; isobutyl chloroformate In acetonitrile at -15 - 0℃;
Stage #2: With benzotriazol-1-ol In N,N-dimethyl-formamide; acetonitrile at -15℃;
Stage #3: Boc-Arg(NO2)-OH In N,N-dimethyl-formamide; acetonitrile at -15 - 20℃; pH=8;
H-Gly-Asp(OBzl)-Ser(Bzl)-OBzl*HCl

H-Gly-Asp(OBzl)-Ser(Bzl)-OBzl*HCl

Boc-Arg(NO2)-OH
2188-18-3

Boc-Arg(NO2)-OH

Boc-Arg(Nω-NO2)-Gly-Asp(OBn)-Ser(Bn)-OBn
246516-47-2

Boc-Arg(Nω-NO2)-Gly-Asp(OBn)-Ser(Bn)-OBn

Conditions
ConditionsYield
Stage #1: Boc-Arg(NO2)-OH With 1-hydroxybenzotriazol-hydrate; dicyclohexyl-carbodiimide In tetrahydrofuran at 0℃; for 0.5h;
Stage #2: H-Gly-Asp(OBzl)-Ser(Bzl)-OBzl*HCl With 4-methyl-morpholine In tetrahydrofuran at 20℃; for 8h; pH=8.5; Further stages.;
89%
Stage #1: Boc-Arg(NO2)-OH With benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran for 0.333333h; Cooling with ice;
Stage #2: H-Gly-Asp(OBzl)-Ser(Bzl)-OBzl*HCl With 4-methyl-morpholine In tetrahydrofuran at 20℃; for 24h;
85%
Boc-Arg(NO2)-OH
2188-18-3

Boc-Arg(NO2)-OH

N,0-dimethylhydroxylamine
1117-97-1

N,0-dimethylhydroxylamine

Nα-(tert-butoxycarbonyl)-L-nitroarginine N-methyl-O-methylcarboxamide
139976-34-4

Nα-(tert-butoxycarbonyl)-L-nitroarginine N-methyl-O-methylcarboxamide

Conditions
ConditionsYield
Stage #1: Boc-Arg(NO2)-OH With N-methylcyclohexylamine; isobutyl chloroformate
Stage #2: N,0-dimethylhydroxylamine With N-methylcyclohexylamine
89%
Boc-Arg(NO2)-OH
2188-18-3

Boc-Arg(NO2)-OH

H-Ala-Ser-OMe
107540-41-0

H-Ala-Ser-OMe

Boc-Arg(NO2)-Ala-Ser-OMe
107540-42-1

Boc-Arg(NO2)-Ala-Ser-OMe

Conditions
ConditionsYield
With 4-methyl-morpholine; benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran 1.) -10 deg C, 1 h, 2.) room temp., 18 h;88%
Boc-Arg(NO2)-OH
2188-18-3

Boc-Arg(NO2)-OH

glycine ethyl ester hydrochloride
5680-79-5

glycine ethyl ester hydrochloride

Boc-Arg(Nω-NO2)-Gly-OCH3
111083-00-2

Boc-Arg(Nω-NO2)-Gly-OCH3

Conditions
ConditionsYield
Stage #1: Boc-Arg(NO2)-OH With benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran at 0℃; under 750.075 Torr; for 0.5h; Inert atmosphere;
Stage #2: glycine ethyl ester hydrochloride With 4-methyl-morpholine In tetrahydrofuran at 0 - 20℃; under 750.075 Torr; pH=8.5; Inert atmosphere;
88%
Stage #1: Boc-Arg(NO2)-OH With benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere;
Stage #2: glycine ethyl ester hydrochloride With 4-methyl-morpholine In tetrahydrofuran at 0 - 20℃; pH=8.5; Inert atmosphere;
88%
Boc-Arg(NO2)-OH
2188-18-3

Boc-Arg(NO2)-OH

1-(tert-butoxycarbonyl)-4-aminopiperidine
87120-72-7

1-(tert-butoxycarbonyl)-4-aminopiperidine

4-({(2S)-2-[(tert-butoxycarbonyl)amino]-5-(3-nitroguanidino)pentanoyl}amino)piperidine-1-carboxylic acid tert-butyl ester

4-({(2S)-2-[(tert-butoxycarbonyl)amino]-5-(3-nitroguanidino)pentanoyl}amino)piperidine-1-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃;87%
Boc-Arg(NO2)-OH
2188-18-3

Boc-Arg(NO2)-OH

tert-butyl (3S)-3-aminopiperidine-1-carboxylate
625471-18-3

tert-butyl (3S)-3-aminopiperidine-1-carboxylate

(3S)-3-({(2S)-2-[(tert-butoxycarbonyl)amino]-5-(3-nitroguanidino)pentanoyl}amino)piperidine-1-carboxylic acid tert-butyl ester

(3S)-3-({(2S)-2-[(tert-butoxycarbonyl)amino]-5-(3-nitroguanidino)pentanoyl}amino)piperidine-1-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃;87%
H-Gly-Asp(OBzl)-Phe-OBzl*HCl

H-Gly-Asp(OBzl)-Phe-OBzl*HCl

Boc-Arg(NO2)-OH
2188-18-3

Boc-Arg(NO2)-OH

Boc-Arg(Nω-NO2)-Gly-Asp(OBn)-Phe-OBn
906673-81-2

Boc-Arg(Nω-NO2)-Gly-Asp(OBn)-Phe-OBn

Conditions
ConditionsYield
Stage #1: Boc-Arg(NO2)-OH With 1-hydroxybenzotriazol-hydrate; dicyclohexyl-carbodiimide In tetrahydrofuran at 0℃; for 0.5h;
Stage #2: H-Gly-Asp(OBzl)-Phe-OBzl*HCl With 4-methyl-morpholine In tetrahydrofuran at 20℃; for 8h; pH=8.5; Further stages.;
87%
Stage #1: Boc-Arg(NO2)-OH With benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran for 0.333333h; Cooling with ice;
Stage #2: H-Gly-Asp(OBzl)-Phe-OBzl*HCl With 4-methyl-morpholine In tetrahydrofuran at 20℃; for 24h;
87%
Boc-Arg(NO2)-OH
2188-18-3

Boc-Arg(NO2)-OH

glycine benzyl ester p-toluenesulfonic acid salt
1738-76-7

glycine benzyl ester p-toluenesulfonic acid salt

Nα-tert-butyloxycarbonyl-NG-nitroarginylglycine benzyl ester
83103-21-3

Nα-tert-butyloxycarbonyl-NG-nitroarginylglycine benzyl ester

Conditions
ConditionsYield
Stage #1: Boc-Arg(NO2)-OH With benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran at 0℃; for 0.5h;
Stage #2: glycine benzyl ester p-toluenesulfonic acid salt With 4-methyl-morpholine In tetrahydrofuran at 0 - 20℃; for 10h; pH=9;
86%
With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In acetonitrile76%
With 4-methyl-morpholine; benzotriazol-1-ol; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide
Boc-Arg(NO2)-OH
2188-18-3

Boc-Arg(NO2)-OH

H-Pro-OBzl
41324-66-7

H-Pro-OBzl

Boc-Arg(NO2)-Pro-OBzl
54046-53-6

Boc-Arg(NO2)-Pro-OBzl

Conditions
ConditionsYield
Stage #1: H-Pro-OBzl With benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran at 0℃; for 24h;
Stage #2: Boc-Arg(NO2)-OH With 4-methyl-morpholine In tetrahydrofuran at 20℃; for 24h;
86%
Boc-Arg(NO2)-OH
2188-18-3

Boc-Arg(NO2)-OH

diazomethyl-trimethyl-silane
18107-18-1

diazomethyl-trimethyl-silane

Nα-(tert-butoxycarbonyl)-NG-nitro-L-arginine methyl ester
112208-06-7

Nα-(tert-butoxycarbonyl)-NG-nitro-L-arginine methyl ester

Conditions
ConditionsYield
In methanol; benzene at 20℃; for 3h; Methylation;85%
In methanol; benzene
Boc-Arg(NO2)-OH
2188-18-3

Boc-Arg(NO2)-OH

Pro-Ala-Lys(Z)-OBzl hydrochloride

Pro-Ala-Lys(Z)-OBzl hydrochloride

Boc-Arg(NO2)-Pro-Ala-Lys(Z)-OBzl
663954-94-7

Boc-Arg(NO2)-Pro-Ala-Lys(Z)-OBzl

Conditions
ConditionsYield
Stage #1: Boc-Arg(NO2)-OH With benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran for 0.333333h; Cooling with ice;
Stage #2: Pro-Ala-Lys(Z)-OBzl hydrochloride With 4-methyl-morpholine In tetrahydrofuran at 20℃; for 24h;
85%
Stage #1: Pro-Ala-Lys(Z)-OBzl hydrochloride With benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran at 0℃; for 24h;
Stage #2: Boc-Arg(NO2)-OH With 4-methyl-morpholine In tetrahydrofuran at 20℃; for 24h;
77%
Boc-Arg(NO2)-OH
2188-18-3

Boc-Arg(NO2)-OH

Arg(NO2)-Pro-Ala-Lys(Z)-OBzl hydrochloride

Arg(NO2)-Pro-Ala-Lys(Z)-OBzl hydrochloride

Boc-Arg(NO2)-Arg(NO2)-Pro-Ala-Lys(Z)-OBzl
713524-13-1

Boc-Arg(NO2)-Arg(NO2)-Pro-Ala-Lys(Z)-OBzl

Conditions
ConditionsYield
Stage #1: Arg(NO2)-Pro-Ala-Lys(Z)-OBzl hydrochloride With benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran at 0℃; for 24h;
Stage #2: Boc-Arg(NO2)-OH With 4-methyl-morpholine In tetrahydrofuran at 20℃; for 24h;
85%
oxime resin

oxime resin

1-(tert-butoxycarbonyl)-L-proline
15761-39-4

1-(tert-butoxycarbonyl)-L-proline

t-Boc-L-valine
13734-41-3

t-Boc-L-valine

N-tert-butoxycarbonyl-L-leucine
13139-15-6

N-tert-butoxycarbonyl-L-leucine

Boc-Arg(NO2)-OH
2188-18-3

Boc-Arg(NO2)-OH

Boc-Orn(Z)-OH
2480-93-5

Boc-Orn(Z)-OH

Boc-D-Phe-OH
18942-49-9

Boc-D-Phe-OH

cyclo[-Val-Orn(Z)-Leu-Arg(NO2)-D-Phe-Pro-Val-Orn(Z)-Leu-D-Phe-Pro-]

cyclo[-Val-Orn(Z)-Leu-Arg(NO2)-D-Phe-Pro-Val-Orn(Z)-Leu-D-Phe-Pro-]

Conditions
ConditionsYield
Stage #1: oxime resin; N-tert-butoxycarbonyl-L-leucine With dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 15h; solid phase reaction;
Stage #2: With trifluoroacetic acid In dichloromethane solid phase reaction;
Stage #3: 1-(tert-butoxycarbonyl)-L-proline; t-Boc-L-valine; N-tert-butoxycarbonyl-L-leucine; Boc-Arg(NO2)-OH; Boc-Orn(Z)-OH; Boc-D-Phe-OH Further stages;
85%
Boc-Arg(NO2)-OH
2188-18-3

Boc-Arg(NO2)-OH

Pro-Gly-Pro benzyl ester trifluoroacetate

Pro-Gly-Pro benzyl ester trifluoroacetate

Boc-Arg(NO2)-Pro-Gly-Pro-OBzl

Boc-Arg(NO2)-Pro-Gly-Pro-OBzl

Conditions
ConditionsYield
Stage #1: Boc-Arg(NO2)-OH With dicyclohexyl-carbodiimide In tetrahydrofuran; N,N-dimethyl-formamide at 0℃; for 0.666667h;
Stage #2: Pro-Gly-Pro benzyl ester trifluoroacetate With triethylamine In tetrahydrofuran; N,N-dimethyl-formamide for 72h;
85%
Boc-Arg(NO2)-OH
2188-18-3

Boc-Arg(NO2)-OH

TFA H-Pro-Gly-Pro-OBzl

TFA H-Pro-Gly-Pro-OBzl

Boc-Arg(NO2)-Pro-Gly-Pro-OBzl

Boc-Arg(NO2)-Pro-Gly-Pro-OBzl

Conditions
ConditionsYield
Stage #1: Boc-Arg(NO2)-OH With dicyclohexyl-carbodiimide In tetrahydrofuran; N,N-dimethyl-formamide at 0℃; for 0.666667h;
Stage #2: TFA H-Pro-Gly-Pro-OBzl With triethylamine In tetrahydrofuran; N,N-dimethyl-formamide for 72h;
85%

2188-18-3Relevant articles and documents

(Nitro) hymenamide A, unusual biologically active cyclic peptide

Belagali,Himaja,Kumar,Thomas,Prakasini,Poojary

, p. 160 - 164 (2007/10/03)

A new biological active cyclic peptide (Nitro) Hymenamide A has been synthesized and the structure was established on the basis of analytical, IR, NMR and mass spectral data. The new compound was subjected to both antimicrobial and pharmacological studies.

Syntheses of N(α)-(β-naphthylsulfonylaminoglycyl)-argininamides as potential selective synthetic thrombin inhibitors

Etemad-Moghadam,Delebassee,Maffrand,Frehel

, p. 577 - 585 (2007/10/02)

-

3-Alkoxycarbonyl-2-oxazolones and Their Homopolymers as Highly Preservable Amino-Protecting Reagents. tert-Butoxy-carbonylation and Benzyloxycarbonylation of Amino Groups

Kunieda, Takehisa,Higuchi, Tsunehiko,Abe, Yoshihiro,Hirobe, Masaaki

, p. 2174 - 2181 (2007/10/02)

Highly preservable amino protecting reagents derived from the 2-oxazolone moiety as a common activating mediator have been developed. 3-Alkoxycarbonyl-2-oxazolones serve as easily handled reagents for amino protection, including tert-butoxycarbonylation, benzyloxycarbonylation, p-methoxybenzyloxycarbonylation, methoxycarbonylation and ethoxycarbonylation.For example, high yield N-protection of α-amino acids has been smoothly performed by the use of 3-tert-butoxycarbonyl and 3-benzyloxycarbonyl-2-oxazolones in aqueous solution at room temperature.A series of homopolymers, poly(3-alkoxycarbonyl-2-oxazolone), is readily obtainable by radical-initiated chain reaction of the corresponding 4,5-unsubstituted oxazolone monomers (except for the tert-butoxy derivate, which failed to give polymeric compounds), and these were successfully used for amino protection as well.Use of the polymer reagents greatly simplifies the purification procedure, though a longer reaction time is required.Keywords - 3-alkoxycarbonyl-2-oxazolone; poly(2-alkoxycarbonyl-2-oxazolone); 3-tert-butoxycarbonyl-2-oxazolone; 3-benzyloxycarbonyl-2-oxazolone; amino protection

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