gamma-Benzyl L-glutamate supplier

Name
gamma-Benzyl L-glutamate
EINECS 216-826-1
CAS No. 1676-73-9
Article Data62
CAS DataBase
Density 1.245 g/cm₃
Solubility
Melting Point 181-182 °C(lit.)
Formula C₁₂H₁₅NO₄
Boiling Point 426.1 °C at 760 mmHg
Molecular Weight 237.255
Flash Point 211.5 °C
Transport Information
Appearance white powder
Safety 22-24/25
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms Glutamicacid, 5-benzyl ester, L- (6CI,8CI);5-Benzyl L-glutamate;Glutamic acid g-benzyl ester;L-Glutamicacid g-benzyl ester;NSC 9969;g-Benzyl glutamate;L-Glutamic acid γ-be;H-Glu(OBzl)-OH;
PSA 89.62000
LogP 1.62220

Synthetic route

: 23506-06-1
Z(OMe)-Glu(OBzl)-OH

: 1676-73-9
L-glutamic acid γ-benzyl ester

Conditions

Conditions	Yield
With methanesulfonic acid; 3-methyl-phenol In dichloromethane at 25℃; for 0.5h;	100%

: 56-86-0
L-glutamic acid

: 100-51-6
benzyl alcohol

A: 1676-73-9
L-glutamic acid γ-benzyl ester

B: 13030-09-6
1-benzyl L-glutamate

Conditions

Conditions	Yield
With copper dichloride at 60℃; for 2h; Catalytic behavior; Mechanism; Reagent/catalyst; Solvent; Temperature;	A 95.31% B n/a

...Expand

: 56-86-0
L-glutamic acid

: 100-51-6
benzyl alcohol

: 1676-73-9
L-glutamic acid γ-benzyl ester

Conditions

Conditions	Yield
With tetrafluoroboric acid diethyl ether; sodium sulfate for 15h; Ambient temperature;	94%
With tetrafluoroboric acid diethyl ether; sodium sulfate at 20℃; for 12h; Inert atmosphere;	80%
Stage #1: L-glutamic acid; benzyl alcohol With methanesulfonic acid In toluene at 30 - 45℃; for 6h; Stage #2: With ammonia In ethanol; water at 60℃; for 2h; pH=6.5 - 7;	77%

: 2768-50-5
dibenzyl L-glutamate

: 1676-73-9
L-glutamic acid γ-benzyl ester

Conditions

Conditions	Yield
With water In acetone at 37℃; for 4h; Alcalase, pH 8.2;	85%
In ethanol; water at 25℃; for 3h; pronase (E C 3.4.24.4.), pH 7.2;	72%
(i) TsOH, (ii) CuSO4*5H2O, aq. NaOH, EtOH, Na2H2edta; Multistep reaction;

: Copper(II); (S)-2-amino-4-benzyloxycarbonyl-butyrate

: 1676-73-9
L-glutamic acid γ-benzyl ester

Conditions

Conditions	Yield
With sodium sulfide In water at 25 - 30℃; for 0.166667h;	84%

: γ-benzyl L-glutamate methanesulphonate

: 1676-73-9
L-glutamic acid γ-benzyl ester

Conditions

Conditions	Yield
With ammonia In water at 13 - 15℃; for 2h; pH=5.9 - 6.3;	81%

: 56-86-0
L-glutamic acid

: 100-39-0
benzyl bromide

: 1676-73-9
L-glutamic acid γ-benzyl ester

Conditions

Conditions	Yield
With copper	70%
Yield given. Multistep reaction;

Oδ-Bzl-L-Glu/copper complex: Oδ-Bzl-L-Glu/copper complex

: 1676-73-9
L-glutamic acid γ-benzyl ester

Conditions

Conditions	Yield
With N,N-Dibutyl-N'-(benzoyl)thioharnstoff In ethanol for 2h; Heating;	60%

: 56-86-0
L-glutamic acid

: 104-15-4
toluene-4-sulfonic acid

: 100-51-6
benzyl alcohol

: 1676-73-9
L-glutamic acid γ-benzyl ester

Conditions

Conditions	Yield
at 120℃; under 2 Torr;

...Expand

: 56-86-0
L-glutamic acid

: 98-11-3
benzenesulfonic acid

: 100-51-6
benzyl alcohol

: 1676-73-9
L-glutamic acid γ-benzyl ester

Conditions

Conditions	Yield
at 100 - 105℃;

...Expand

: 100-39-0
benzyl bromide

: 3-((S)-2,2-Diethyl-5-oxo-4,5-dihydro-3λ5,2λ5-[1,3,2]oxazaborol-4-yl)-propionic acid

: 1676-73-9
L-glutamic acid γ-benzyl ester

Conditions

Conditions	Yield
With hydrogenchloride; N-cyclohexyl-cyclohexanamine 1) DMF, 60-70 degC, 5 min; 2) EtOAc; Yield given. Multistep reaction;

: 620-05-3
iodomethylbenzene

: 2C5H7NO4(2-)*Cu(2+)*2Na(1+)

: 1676-73-9
L-glutamic acid γ-benzyl ester

Conditions

Conditions	Yield
In water; N,N-dimethyl-formamide

: 2791-84-6
L-glutamic acid dibenzyl ester 4-toluenesulfonate

: 1676-73-9
L-glutamic acid γ-benzyl ester

Conditions

Conditions	Yield
With ethylenediaminetetraacetic acid; water; copper(II) sulfate 1.) EtOH, 32 deg C, 60 min, 2.) EtOH, 100 deg C; Yield given; Multistep reaction;

: 56-86-0
L-glutamic acid

: 1676-73-9
L-glutamic acid γ-benzyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 72 percent / benzene / Heating 2: 1.) CuSO4*5H2O, H2O, 2.) EDTA, H2O / 1.) EtOH, 32 deg C, 60 min, 2.) EtOH, 100 deg C View Scheme

: 104-15-4
toluene-4-sulfonic acid

4-polystyryltriphenylmethyl-Phe-ODpm: 4-polystyryltriphenylmethyl-Phe-ODpm

: 1676-73-9
L-glutamic acid γ-benzyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 72 percent / benzene / Heating 2: 1.) CuSO4*5H2O, H2O, 2.) EDTA, H2O / 1.) EtOH, 32 deg C, 60 min, 2.) EtOH, 100 deg C View Scheme

: 6893-26-1
D-Glutamic acid

: 100-51-6
benzyl alcohol

: 1676-73-9
L-glutamic acid γ-benzyl ester

Conditions

Conditions	Yield
With sulfuric acid at 70℃;

: 1676-73-9
L-glutamic acid γ-benzyl ester

: 24424-99-5
di-tert-butyl dicarbonate

: 13574-13-5
Boc-Glu(OBzl)-OH

Conditions

Conditions	Yield
In 1,4-dioxane; water at 0℃;	100%
In 1,4-dioxane; water at 0℃;	100%
With triethylamine In N,N-dimethyl-formamide at 60℃; for 0.5h;	98%

: 1676-73-9
L-glutamic acid γ-benzyl ester

: 56-86-0
L-glutamic acid

Conditions

Conditions	Yield
With dimethylsulfide; hydrogen fluoride; methoxybenzene at 0℃; for 1h; Product distribution; Rate constant; other concentration of reagents;	100%
With dimethylsulfide; trifluorormethanesulfonic acid; 30 (v/v); trifluoroacetic acid at 0℃; for 4h; Yield given;
With trifluoroacetic acid In dichloromethane at 20℃; Rate constant;
With recombinant Pseudomonas nitroreducens IFO12694 γ-glutamyltranspeptidase at 30℃; for 0.0333333h; pH=10.5; aq. buffer; Enzymatic reaction;
With E. coli BL21 Star (DE3) S30 extract In aq. buffer at 37℃; for 6h; pH=7.5;

: 1676-73-9
L-glutamic acid γ-benzyl ester

: 3392-05-0
Boc-Ala-O-N-hydroxysuccinimide

: 17080-23-8
Boc-Ala-Glu(OBzl)-OH

Conditions

Conditions	Yield
With 4-methyl-morpholine In 2,3,7,8-Tetrachloro-dibenzo[1,4]dioxine; water at 20℃; for 12 - 18h; pH=~ 9 - 9.2;	100%
With potassium hydrogencarbonate In tetrahydrofuran; water at 20℃;
With 4-methyl-morpholine In 1,4-dioxane; water at 20℃; for 12h;

: 1676-73-9
L-glutamic acid γ-benzyl ester

: 132307-50-7
2,5-dioxopyrrolidin-1-yl N2-(((9H-fluoren-9-yl)methoxy)carbonyl)-N6-(tert-butoxycarbonyl)-L-lysinate

: 1006066-87-0
Fmoc-L-Lys(Boc)-L-Glu(OBzl)-OH

Conditions

Conditions	Yield
With 4-methyl-morpholine In 2,3,7,8-Tetrachloro-dibenzo[1,4]dioxine; water at 20℃; for 12 - 18h; pH=~ 9 - 9.2;	100%

: 3392-09-4
Boc-Leu-ONSu

: 1676-73-9
L-glutamic acid γ-benzyl ester

: 32945-71-4
Boc-Leu-Glu(OBzl)-OH

Conditions

Conditions	Yield
With 4-methyl-morpholine In 1,4-dioxane; water at 20℃; for 12h;	100%
With potassium hydrogencarbonate In tetrahydrofuran; water at 20℃;

: 1676-73-9
L-glutamic acid γ-benzyl ester

: 22509-74-6
N-ethoxycarbonylphthalimide

: 88784-33-2
(2S)-4-benzyloxicarbonyl-2-phthalimidobutanoic acid

Conditions

Conditions	Yield
With TEA In tetrahydrofuran Heating;	98%
With sodium carbonate

: 1676-73-9
L-glutamic acid γ-benzyl ester

: benzyl-3-(3H-diazirin-3-yl)propanoate

Conditions

Conditions	Yield
With [bis(acetoxy)iodo]benzene; ammonia In methanol at 0 - 20℃; for 2h; Inert atmosphere;	98%

polystyrene-NHCH2CH2N(CH2CH2NH2)2, Mn = 2180, Mw/Mn = 1.15: polystyrene-NHCH2CH2N(CH2CH2NH2)2, Mn = 2180, Mw/Mn = 1.15

: 1676-73-9
L-glutamic acid γ-benzyl ester

(polystyrene)25-NHCH2CH2N(CH2CH2NH-(γ-benzyl-L-glutamate)51)2, Mn = 7460, Mw/Mn = 1.26: (polystyrene)25-NHCH2CH2N(CH2CH2NH-(γ-benzyl-L-glutamate)51)2, Mn = 7460, Mw/Mn = 1.26

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 24h;	97%

: 75-44-5
phosgene

: 1676-73-9
L-glutamic acid γ-benzyl ester

: 3190-71-4
5-benzyl L-glutamate N-carboxyanhydride

Conditions

Conditions	Yield
In tetrahydrofuran; toluene at 50℃; for 1h;	95.4%
In tetrahydrofuran; toluene at 50℃; for 1.16h;	95.4%
In tetrahydrofuran at 50℃; for 3h; Inert atmosphere;	93.5%

: 32315-10-9
bis(trichloromethyl) carbonate

: 1676-73-9
L-glutamic acid γ-benzyl ester

: 3190-71-4
5-benzyl L-glutamate N-carboxyanhydride

Conditions

Conditions	Yield
In tetrahydrofuran at 40℃; Inert atmosphere;	95.1%
at 50℃; for 12h; Inert atmosphere;	94%
In ethyl acetate for 3h; Inert atmosphere; Reflux;	92%

: 1676-73-9
L-glutamic acid γ-benzyl ester

: 503-38-8
trichloromethyl chloroformate

: 3190-71-4
5-benzyl L-glutamate N-carboxyanhydride

Conditions

Conditions	Yield
With sodium hydroxide In tetrahydrofuran; ethanol; water for 1.5h; Inert atmosphere; Reflux;	95%
In tetrahydrofuran for 1.5h; Inert atmosphere; Reflux;	95%
In tetrahydrofuran at 70℃; Inert atmosphere;	95%

: 2899-60-7
Cbz-Gly-ONSuc

: 1676-73-9
L-glutamic acid γ-benzyl ester

: 100736-69-4
Z-Gly-Glu(OBzl)-OH

Conditions

Conditions	Yield
With calcium(II) nitrate; triethylamine In N,N-dimethyl-formamide at 20℃; for 2h; Condensation;	94%

: 1676-73-9
L-glutamic acid γ-benzyl ester

: 769922-77-2
(S)-benzyl (1-(1H-benzo[d][1,2,3]triazol-1-yl)-1-oxo-3-phenylpropan-2-yl)carbamate

: 14297-16-6
Cbz-L-Phe-L-Glu(OBn)-OH

Conditions

Conditions	Yield
With triethylamine In water; acetonitrile	93%

: 1676-73-9
L-glutamic acid γ-benzyl ester

: 117679-91-1
1-O-benzyl 4-O-(2,-5-dioxopyrrolidin-1-yl) butanedioate

: N-benzylsuccinyl-γ-benzyl-glutamic acid

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0 - 20℃; for 18h;	93%

: 67-56-1
methanol

: 1676-73-9
L-glutamic acid γ-benzyl ester

: 41089-47-8
L-glutamic acid α-methyl γ-benzyl diester hydrochloride

Conditions

Conditions	Yield
With thionyl chloride at 0 - 22℃;	92%

: 3392-12-9
Boc-Val-ONSu

: 1676-73-9
L-glutamic acid γ-benzyl ester

: Boc-Val-Glu(OBzl)-OH

Conditions

Conditions	Yield
With 4-methyl-morpholine In 1,4-dioxane; water at 20℃; for 12h;	92%

: 1676-73-9
L-glutamic acid γ-benzyl ester

: 820239-42-7
benzyl N-[(1S)-2-(1H-1,2,3-benzotriazol-1-yl)-1-methyl-2-oxoethyl]carbamate

: Cbz-L-Ala-L-Glu(OBn)-OH

Conditions

Conditions	Yield
With triethylamine In water; acetonitrile	91%

: 32315-10-9
bis(trichloromethyl) carbonate

: 1676-73-9
L-glutamic acid γ-benzyl ester

: C12H14ClNO3

Conditions

Conditions	Yield
In tetrahydrofuran at 60℃; for 3h;	90%

: 1676-73-9
L-glutamic acid γ-benzyl ester

: 3190-71-4
5-benzyl L-glutamate N-carboxyanhydride

Conditions

Conditions	Yield
With phosgene In tetrahydrofuran at 45 - 65℃; for 1.08333h;	89.2%
With phosgene In tetrahydrofuran; toluene for 8h; Ambient temperature;	88.3%
Multi-step reaction with 2 steps 1: aqueous KHCO3 2: PCl5 View Scheme
With bis(trichloromethyl) carbonate; α-pinene In ethyl acetate at 105℃;
With bis(trichloromethyl) carbonate

: 1676-73-9
L-glutamic acid γ-benzyl ester

: 98-79-3
L-Pyroglutamic acid

Conditions

Conditions	Yield
With triethylamine In water; N,N-dimethyl-formamide at 40℃; for 20h;	88.3%

: 1676-73-9
L-glutamic acid γ-benzyl ester

: 501-53-1
benzyl chloroformate

: 5680-86-4
N-benzyloxycarbonyl-5-O-benzyl-L-glutamic acid

Conditions

Conditions	Yield
With sodium hydrogencarbonate for 18h; Ambient temperature;	88%
With sodium hydrogencarbonate In tetrahydrofuran; water at 20℃; for 1h;	86%
With potassium hydrogencarbonate
With potassium carbonate
With sodium hydrogencarbonate In diethyl ether

: 32315-10-9
bis(trichloromethyl) carbonate

: 1676-73-9
L-glutamic acid γ-benzyl ester

: 5254-51-3, 3190-71-4, 10289-08-4, 13822-45-2
3-(2,5-dioxo-oxazolidin-4-yl)-propionic acid benzyl ester

Conditions

Conditions	Yield
In tetrahydrofuran at 65℃; for 2h;	87.6%
In tetrahydrofuran at 50℃; for 3h; Inert atmosphere;	49%
In tetrahydrofuran at 45℃; for 3h;

: 5840-76-6
sarcosine-N-carboxyanhydride

: 5813-64-9
2,2-dimethylpropylamine

: D-glutamic acid benzyl ester-N-carboxylic anhydride

: 1676-73-9
L-glutamic acid γ-benzyl ester

Sar125-b-p-[D-Glu(OBn)15-co-L-Glu(OBn)15]: Sar125-b-p-[D-Glu(OBn)15-co-L-Glu(OBn)15]

Conditions

Conditions	Yield
Stage #1: sarcosine-N-carboxyanhydride; 2.2-dimethylpropylamine In N,N-dimethyl-formamide for 20h; Darkness; Stage #2: D-glutamic acid benzyl ester-N-carboxylic anhydride; L-glutamic acid γ-benzyl ester In N,N-dimethyl-formamide at 25℃; for 24h;	86%

...Expand

: 5840-76-6
sarcosine-N-carboxyanhydride

: 5813-64-9
2,2-dimethylpropylamine

: D-glutamic acid benzyl ester-N-carboxylic anhydride

: 1676-73-9
L-glutamic acid γ-benzyl ester

Sar175-b-p-[D-Glu(OBn)25-co-L-Glu(OBn)25]: Sar175-b-p-[D-Glu(OBn)25-co-L-Glu(OBn)25]

Conditions

Conditions	Yield
Stage #1: sarcosine-N-carboxyanhydride; 2.2-dimethylpropylamine In N,N-dimethyl-formamide for 20h; Darkness; Stage #2: D-glutamic acid benzyl ester-N-carboxylic anhydride; L-glutamic acid γ-benzyl ester In N,N-dimethyl-formamide at 25℃; for 24h;	86%

...Expand

: 5840-76-6
sarcosine-N-carboxyanhydride

: 5813-64-9
2,2-dimethylpropylamine

: D-glutamic acid benzyl ester-N-carboxylic anhydride

: 1676-73-9
L-glutamic acid γ-benzyl ester

Sar175-b-p-[D-Glu(OBn)25-co-L-Glu(OBn)25]: Sar175-b-p-[D-Glu(OBn)25-co-L-Glu(OBn)25]

Conditions

Conditions	Yield
Stage #1: sarcosine-N-carboxyanhydride; 2.2-dimethylpropylamine In water; N,N-dimethyl-formamide; isopropyl alcohol for 20h; Darkness; Stage #2: D-glutamic acid benzyl ester-N-carboxylic anhydride; L-glutamic acid γ-benzyl ester In N,N-dimethyl-formamide at 25℃; for 24h;	86%

...Expand

: 75-44-5
phosgene

: 1676-73-9
L-glutamic acid γ-benzyl ester

: γ-benzyl L-glutamate N-carboxyanhydride

Conditions

Conditions	Yield
In tetrahydrofuran at 45 - 48℃; for 4h;	84.7%

gamma-Benzyl L-glutamate Specification

The IUPAC name of gamma-Benzyl L-glutamate is 2-amino-5-oxo-5-phenylmethoxypentanoic acid . With the CAS registry number 1676-73-9, it is also named as 5-Benzyl L-glutamate ; Glutamic acid gamma-benzyl ester ; L-Glutamic acid 5-benzyl ester ; L-Glutamic acid gamma-benzyl ester ; NSC 9969 ; Benzyl hydrogen gamma-L-glutamate ; Glutamic acid, 5-benzyl ester, L- (8CI) .

The gamma-Benzyl L-glutamate is white powder with slightly sweet flavor. It can be soluble in methanol , ethanol , ether , benzene , acetone , chloroform and ethyl acetate . The product must be stored at the temperature of 2-8 °C. The product's categories are Amino Acids Derivatives, API intermediates, Amino Acids and Glutamic acid [Glu, E]. It is toxic if swallowed. So people should not breathe dust and must avoid contact with skin and eyes.

This product can be used in medicine, food and organic synthesis. It can change to glycosaminoglycan which is the precursor of a mucin synthesis in the body, and can promote ulcer healing. It is mainly used for peptic ulcer drugs. In addition, the product can be used to improve brain function and for the treatment of alcoholism.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 1.56 ; (2)# of Rule of 5 Violations: 0 ; (3)ACD/LogD (pH 5.5): -0.94 ; (4)ACD/LogD (pH 7.4): -0.95 ; (5)ACD/BCF (pH 5.5): 1 ; (6)ACD/BCF (pH 7.4): 1 ; (7)ACD/KOC (pH 5.5): 1 ; (8)ACD/KOC (pH 7.4): 1 ; (9)#H bond acceptors: 5 ; (10)#H bond donors: 3 ; (11)#Freely Rotating Bonds: 8 ; (12)Index of Refraction: 1.555 ; (13)Molar Refractivity: 61.16 cm³ ; (14)Molar Volume: 190.4 cm³ ; (15)Polarizability: 24.24×10^-24 cm³ ; (16)Surface Tension: 53.8 dyne/cm ; (17)Enthalpy of Vaporization: 71.78 kJ/mol ; (18)Vapour Pressure: 5.08E-08 mmHg at 25°C ; (19)Rotatable Bond Count: 7 ; (20)Exact Mass: 237.100108 ; (21)MonoIsotopic Mass: 237.100108 ; (22)Topological Polar Surface Area: 89.6 ; (23)Heavy Atom Count: 17.

People can use the following data to convert to the molecule structure. SMILES: O=C(O)[C@@H](N)CCC(=O)OCc1ccccc1; InChI: InChI=1/C12H15NO4/c13-10(12(15)16)6-7-11(14)17-8-9-4-2-1-3-5-9/h1-5,10H,6-8,13H2,(H,15,16)/t10-/m0/s1.

Product Name

gamma-Benzyl L-glutamate

Synthetic route

gamma-Benzyl L-glutamate Specification

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