Boc-L-glutamic acid 5-cyclohexyl ester supplier

Name
Boc-L-glutamic acid 5-cyclohexyl ester
EINECS
CAS No. 73821-97-3
Article Data2
CAS DataBase
Density 1.16 g/cm³
Solubility
Melting Point 54-57 °C
Formula C₁₆H₂₇NO₆
Boiling Point 502.6 °C at 760 mmHg
Molecular Weight 329.393
Flash Point 257.8 °C
Transport Information
Appearance white powder
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms N-tert-Butoxycarbonyl-L-glutamicacid g-cyclohexyl ester;N-tert-Butyloxycarbonyl-L-glutamic acid g-cyclohexyl ester;Boc-Glu(OcHex)-OH;
PSA 101.93000
LogP 3.01130

Synthetic route

N-Boc-Glu(OcHex)-PAM resin: N-Boc-Glu(OcHex)-PAM resin

N-α-tert-butyloxycarbonyl-glutamic acid, γ-cyclohexyl ester: N-α-tert-butyloxycarbonyl-glutamic acid, γ-cyclohexyl ester

Conditions

Conditions	Yield
With trimethyltin(IV) hydroxide In 1,2-dichloro-ethane for 10h; Heating;	100%

N-Boc-Glu(OcHex)-Merrifield resin: N-Boc-Glu(OcHex)-Merrifield resin

: 73821-97-3
N-α-tert-butyloxycarbonyl-glutamic acid, γ-cyclohexyl ester

Conditions

Conditions	Yield
With trimethyltin(IV) hydroxide In 1,2-dichloro-ethane for 12h; Heating;	97%

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

: 112471-82-6
γ-cyclohexyl L-glutamate

: 73821-97-3
N-α-tert-butyloxycarbonyl-glutamic acid, γ-cyclohexyl ester

Conditions

Conditions	Yield
With N,N,N',N'-tetramethylguanidine In N,N-dimethyl-formamide for 12h; Ambient temperature; Yield given;

: 56-86-0
L-glutamic acid

: 73821-97-3
N-α-tert-butyloxycarbonyl-glutamic acid, γ-cyclohexyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: H2SO4 / diethyl ether / 2 h / 70 °C 2: 1,1,3,3-tetramethylguanidine / dimethylformamide / 12 h / Ambient temperature View Scheme

: 108-93-0
cyclohexanol

nitrogen: nitrogen

: 73821-97-3
N-α-tert-butyloxycarbonyl-glutamic acid, γ-cyclohexyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: H2SO4 / diethyl ether / 2 h / 70 °C 2: 1,1,3,3-tetramethylguanidine / dimethylformamide / 12 h / Ambient temperature View Scheme

: 73821-97-3
N-α-tert-butyloxycarbonyl-glutamic acid, γ-cyclohexyl ester

: 56-86-0
L-glutamic acid

Conditions

Conditions	Yield
With phenylthiotrimethylsilane; pertrimethylsilylated Nafion; 3-methyl-phenol; trifluoroacetic acid for 3h;	100%

: 73821-97-3
N-α-tert-butyloxycarbonyl-glutamic acid, γ-cyclohexyl ester

: 162463-99-2
(S)-2-azido-3-hydroxypropionic acid methyl ester

: 940950-90-3
methyl (2S,2'S)-2-azido-3-(N-Boc-ω-cyclohexyl-glutamyloxy)propionate

Conditions

Conditions	Yield
With dmap; diisopropyl-carbodiimide In dichloromethane at 0 - 20℃;	99%
Stage #1: N-α-tert-butyloxycarbonyl-glutamic acid, γ-cyclohexyl ester With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0℃; for 0.25h; Inert atmosphere; Stage #2: (S)-2-azido-3-hydroxypropionic acid methyl ester In dichloromethane at 0 - 20℃; Inert atmosphere;	99%

: 73821-97-3
N-α-tert-butyloxycarbonyl-glutamic acid, γ-cyclohexyl ester

: (S)-2-[(S)-2-((S)-2-{(S)-2-[(S)-2-((S)-2-Amino-4-carbamoyl-butyrylamino)-4-cyclohexyloxycarbonyl-butyrylamino]-6-benzyloxycarbonylamino-hexanoylamino}-4-carbamoyl-butyrylamino)-propionylamino]-6-benzyloxycarbonylamino-hexanoic acid benzyl ester

: 114855-99-1
Boc-Glu(OcHex)-Gln-Glu(OcHex)-Lys(Z)-Gln-Ala-Lys(Z)-OBzl

Conditions

Conditions	Yield
With 4-methyl-morpholine; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In N,N-dimethyl-formamide at 4℃; for 8h;	96%

: 73821-97-3
N-α-tert-butyloxycarbonyl-glutamic acid, γ-cyclohexyl ester

: H-Tfeg-Tfeg-Lys(ClZ)-OTce*HCl

: 266325-39-7
Boc-Glu(OcHex)-Tfeg-Tfeg-Lys(ClZ)-OTce

Conditions

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 0 - 20℃; Acylation;	96%

: 73821-97-3
N-α-tert-butyloxycarbonyl-glutamic acid, γ-cyclohexyl ester

: TFA*Ser-OBn

: Boc-Glu(OcHx)-Ser-OBzl

Conditions

Conditions	Yield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 6h;	96%

: 73821-97-3
N-α-tert-butyloxycarbonyl-glutamic acid, γ-cyclohexyl ester

: H-Ala-Glu(O-Chx)-Lys(2-Adoc)-Cys(MeBzl)-OBzl*TFA

: Boc-Glu(O-Chx)-Ala-Glu(O-Chx)-Lys(2-Adoc)-Cys(MeBzl)-OBzl

Conditions

Conditions	Yield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine In dichloromethane for 2h; Ambient temperature;	95.1%

: 73821-97-3
N-α-tert-butyloxycarbonyl-glutamic acid, γ-cyclohexyl ester

: 138848-57-4
Boc-Glu(OcHx)-NH2

Conditions

Conditions	Yield
Stage #1: N-α-tert-butyloxycarbonyl-glutamic acid, γ-cyclohexyl ester With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 0.333333h; Stage #2: With ammonium hydroxide In dichloromethane for 1.5h; Further stages.;	95%

: 73821-97-3
N-α-tert-butyloxycarbonyl-glutamic acid, γ-cyclohexyl ester

: 2419-94-5
Boc-Glu

Conditions

Conditions	Yield
With magnesium; hydrazinium monoformate In methanol at 25℃; for 2h;	94%

: 73821-97-3
N-α-tert-butyloxycarbonyl-glutamic acid, γ-cyclohexyl ester

: (S)-2-{(S)-2-[(S)-2-((S)-2-Amino-6-benzyloxycarbonylamino-hexanoylamino)-4-carbamoyl-butyrylamino]-propionylamino}-6-benzyloxycarbonylamino-hexanoic acid benzyl ester

: 114856-05-2
Boc-Glu(OcHex)-Lys(Z)-Gln-Ala-Lys(Z)-OBzl

Conditions

Conditions	Yield
With 4-methyl-morpholine; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In N,N-dimethyl-formamide at 4℃; for 8h;	91%

: 4530-20-5
BOC-glycine

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

: 33640-54-9
N-Boc-Lys(ClZ)-OH

: 73821-97-3
N-α-tert-butyloxycarbonyl-glutamic acid, γ-cyclohexyl ester

Boc-Ala-His(Bom)-Ala-(p-nitrobenzophenone oxime resin)C6H5CH2OC(O)X: Boc-Ala-His(Bom)-Ala-(p-nitrobenzophenone oxime resin)C6H5CH2OC(O)X

: Boc-Ala-His(Bom)-Ala-Glu(OcHex)-Leu-Leu-Lys(ClZ)-Gly-OBzl

Conditions

Conditions	Yield
Multistep reaction;	91%

...Expand

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

: 15761-38-3
L-N-Boc-Ala

: 33640-54-9
N-Boc-Lys(ClZ)-OH

: 73821-97-3
N-α-tert-butyloxycarbonyl-glutamic acid, γ-cyclohexyl ester

Conditions

Conditions	Yield
Multistep reaction;	91%

...Expand

N-tert-butoxycarbonyl-L-leucine: N-tert-butoxycarbonyl-L-leucine

: 15761-38-3
L-N-Boc-Ala

: 33640-54-9
N-Boc-Lys(ClZ)-OH

: 73821-97-3
N-α-tert-butyloxycarbonyl-glutamic acid, γ-cyclohexyl ester

Boc-D-Ala-Pro-(p-nitrobenzophenone oxime resin): Boc-D-Ala-Pro-(p-nitrobenzophenone oxime resin)

: Boc-D-Ala-Pro-Ala-Glu(OcHex)-Leu-Leu-Lys(ClZ)-OH

Conditions

Conditions	Yield
Multistep reaction;	91%

...Expand

: 73821-97-3
N-α-tert-butyloxycarbonyl-glutamic acid, γ-cyclohexyl ester

: 70-11-1
α-bromoacetophenone

: 123167-66-8
Boc-Glu(OcHex)-OPac

Conditions

Conditions	Yield
With triethylamine In ethyl acetate	89%
With caesium carbonate 1.) EtOH, H2O, 2.) DMF, RT; Yield given. Multistep reaction;

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

: 15761-38-3
L-N-Boc-Ala

: 33640-54-9
N-Boc-Lys(ClZ)-OH

: 73821-97-3
N-α-tert-butyloxycarbonyl-glutamic acid, γ-cyclohexyl ester

Boc-Ala-D-Ala-Pro-(p-nitrobenzophenone oxime resin): Boc-Ala-D-Ala-Pro-(p-nitrobenzophenone oxime resin)

: Boc-Ala-D-Ala-Pro-Ala-Val-Glu(OcHex)-Val-Lys(ClZ)-Val-Ala-OH

Conditions

Conditions	Yield
Multistep reaction;	88%

...Expand

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

: 15761-38-3
L-N-Boc-Ala

: 33640-54-9
N-Boc-Lys(ClZ)-OH

: 73821-97-3
N-α-tert-butyloxycarbonyl-glutamic acid, γ-cyclohexyl ester

Z-Ala-D-Ala-Pro-Ala--(p-nitrobenzophenone oxime resin): Z-Ala-D-Ala-Pro-Ala--(p-nitrobenzophenone oxime resin)

: Z-Ala-D-Ala-Pro-Ala-Orn[4-(10,15,20-tritolylporphyrin-5-yl)benzoyl]-Glu(OcHex)-Val-Lys(ClZ)-Val-Ala-OH

Conditions

Conditions	Yield
Multistep reaction;	88%

...Expand

: 73821-97-3
N-α-tert-butyloxycarbonyl-glutamic acid, γ-cyclohexyl ester

: 75-31-0
isopropylamine

: Boc-L-Glu(OcHx)-NH-i-Pr

Conditions

Conditions	Yield
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine In chloroform	88%

: 73821-97-3
N-α-tert-butyloxycarbonyl-glutamic acid, γ-cyclohexyl ester

: H-Lys(2-Adoc)-Gln-Lys(2-Adoc)-OBzl*HCl

: 249302-38-3
Boc-Glu(O-cHex)-Lys(2-Adoc)-Gln-Lys(2-Adoc)-OBzl

Conditions

Conditions	Yield
With benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 4℃; Acylation;	84.5%

: 73821-97-3
N-α-tert-butyloxycarbonyl-glutamic acid, γ-cyclohexyl ester

: H-Lys(2-Adoc)-Cys(MeBzl)-OBzl*TFA

: Boc-Glu(O-Chx)-Lys(2-Adoc)-Cys(MeBzl)-OBzl

Conditions

Conditions	Yield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine In dichloromethane for 2h; Ambient temperature;	79.8%

: 29022-11-5
N-(fluoren-9-ylmethoxycarbonyl)glycine

: 86060-82-4
Fmoc-Lys(Z)-OH

: 73821-97-3
N-α-tert-butyloxycarbonyl-glutamic acid, γ-cyclohexyl ester

: Boc-Glu(OcHx)GlyLys(Z)-OH

Conditions

Conditions	Yield
Multistep reaction;	79%

...Expand

: 73821-97-3
N-α-tert-butyloxycarbonyl-glutamic acid, γ-cyclohexyl ester

: N'-((S)-2-{(S)-2-[(S)-2-((S)-2-Amino-3-methyl-butyrylamino)-3-carbamoyl-propionylamino]-3-benzyloxy-propionylamino}-3-phenyl-propionyl)-hydrazinecarboxylic acid 2,2,2-trichloro-ethyl ester

: Boc-Glu(OcHex)-Ile-Asn-Ser(Bzl)-Phe-NHNH-Troc

Conditions

Conditions	Yield
With 4-methyl-morpholine; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In N,N-dimethyl-formamide at 4℃; for 8h;	78%

: 53100-33-7
L-Ala-OPAc

: 73821-97-3
N-α-tert-butyloxycarbonyl-glutamic acid, γ-cyclohexyl ester

: 141795-10-0
Boc-Glu(OcHex)-Ala-OPac

Conditions

Conditions	Yield
With benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide In tetrahydrofuran	77%

: 73821-97-3
N-α-tert-butyloxycarbonyl-glutamic acid, γ-cyclohexyl ester

: H-Glu(O-Chx)-Gly-OBzl*TFA

: Boc-Glu(O-Chx)-Glu(O-Chx)-Gly-OBzl

Conditions

Conditions	Yield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine In dichloromethane for 3h; Ambient temperature;	72.9%

: 4530-20-5
BOC-glycine

: 3744-87-4, 7764-95-6, 15761-38-3
Boc-(R)-Ala

: 13734-34-4
N-tert-butoxycarbonyl-L-phenylalanine

: 15260-10-3
N-Boc-O-benzyl-L-threonine

: 13836-37-8
Boc-Arg(Tos)-OH

: 23680-31-1
BOC-O-benzyl-L-serine

: 73821-95-1
Boc-Asp(O-cyclohexyl)-OH

: 73821-97-3
N-α-tert-butyloxycarbonyl-glutamic acid, γ-cyclohexyl ester

: 54613-99-9
Boc-(S)-Lys(2-Cl-Z)-OH

: 47689-67-8
(S)-3-[4-(2-Bromo-benzyloxycarbonyloxy)-phenyl]-2-tert-butoxycarbonylamino-propionic acid

: 83468-83-1
N(α)-t-butoxycarbonyl-N(ϖ)-benzyloxymethyl-L-histidine

H-HAEGTFTSDVSSYLEGQA-[D-Ala]-CKEFIAWLVKGR-NH2: H-HAEGTFTSDVSSYLEGQA-[D-Ala]-CKEFIAWLVKGR-NH2

Conditions

Conditions	Yield
Stage #1: Boc-Arg(Tos)-OH With 6-chloro-3-((dimethylamino)(dimethyliminio)methyl)-1H-benzo[d][1,2,3]triazol-3-ium-1-olatehexafluorophosphate(V); N-ethyl-N,N-diisopropylamine; 6-chloro-1-hydroxybenzotriazole In 1-methyl-pyrrolidin-2-one for 0.5h; solid phase reaction; Stage #2: With trifluoroacetic acid In 1-methyl-pyrrolidin-2-one solid phase reaction; Stage #3: BOC-glycine; Boc-(R)-Ala; N-tert-butoxycarbonyl-L-phenylalanine; N-Boc-O-benzyl-L-threonine; BOC-O-benzyl-L-serine; Boc-Asp(O-cyclohexyl)-OH; N-α-tert-butyloxycarbonyl-glutamic acid, γ-cyclohexyl ester; Boc-(S)-Lys(2-Cl-Z)-OH; (S)-3-[4-(2-Bromo-benzyloxycarbonyloxy)-phenyl]-2-tert-butoxycarbonylamino-propionic acid; N(α)-t-butoxycarbonyl-N(ϖ)-benzyloxymethyl-L-histidine Further stages;	71%

Yield

Stage #1: Boc-Arg(Tos)-OH With 6-chloro-3-((dimethylamino)(dimethyliminio)methyl)-1H-benzo[d][1,2,3]triazol-3-ium-1-olatehexafluorophosphate(V); N-ethyl-N,N-diisopropylamine; 6-chloro-1-hydroxybenzotriazole In 1-methyl-pyrrolidin-2-one for 0.5h; solid phase reaction;
Stage #2: With trifluoroacetic acid In 1-methyl-pyrrolidin-2-one solid phase reaction;
Stage #3: BOC-glycine; Boc-(R)-Ala; N-tert-butoxycarbonyl-L-phenylalanine; N-Boc-O-benzyl-L-threonine; BOC-O-benzyl-L-serine; Boc-Asp(O-cyclohexyl)-OH; N-α-tert-butyloxycarbonyl-glutamic acid, γ-cyclohexyl ester; Boc-(S)-Lys(2-Cl-Z)-OH; (S)-3-[4-(2-Bromo-benzyloxycarbonyloxy)-phenyl]-2-tert-butoxycarbonylamino-propionic acid; N(α)-t-butoxycarbonyl-N(ϖ)-benzyloxymethyl-L-histidine Further stages;

71%

...Expand

: 1738-68-7
Gly-OBz

: 73821-97-3
N-α-tert-butyloxycarbonyl-glutamic acid, γ-cyclohexyl ester

: 142828-14-6
(S)-4-(Benzyloxycarbonylmethyl-carbamoyl)-4-tert-butoxycarbonylamino-butyric acid cyclohexyl ester

Conditions

Conditions	Yield
With benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 4℃;	70%
With 4-methyl-morpholine; isobutyl chloroformate

: 73821-97-3
N-α-tert-butyloxycarbonyl-glutamic acid, γ-cyclohexyl ester

: 100-39-0
benzyl bromide

: 73821-96-2
(2S)-tert-butoxycarbonylamino-pentanedioic acid 1-benzyl ester 5-cyclohexyl ester

Conditions

Conditions	Yield
With caesium carbonate In methanol	70%
With triethylamine In N,N-dimethyl-formamide at 25℃; for 5h;	67%

: 73821-97-3
N-α-tert-butyloxycarbonyl-glutamic acid, γ-cyclohexyl ester

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

: 142828-14-6
(S)-4-(Benzyloxycarbonylmethyl-carbamoyl)-4-tert-butoxycarbonylamino-butyric acid cyclohexyl ester

Conditions

Conditions	Yield
With benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 4℃;	66.9%

: 73821-97-3
N-α-tert-butyloxycarbonyl-glutamic acid, γ-cyclohexyl ester

: H-Lys(2-Adoc)-Asp(O-2-Ada)-Ala-Pro-OBzl*HCl

: 249302-47-4
Boc-Glu(O-cHex)-Lys(2-Adoc)-Asp(O-2-Ada)-Ala-Pro-OBzl

Conditions

Conditions	Yield
With benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 4℃; Acylation;	64.7%

Boc-L-glutamic acid 5-cyclohexyl ester Chemical Properties

IUPAC Name: 5-Cyclohexyloxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]-5-oxopentanoicacid
Following is the structure of L-Glutamic acid,N-[(1,1-dimethylethoxy)carbonyl]-, 5-cyclohexyl ester (CAS NO.73821-97-3):

Empirical Formula: C₁₆H₂₇NO₆
Molecular Weight: 329.3887
Index of Refraction: 1.497
Molar Refractivity: 83.06 cm³
Molar Volume: 283.4 cm³
Density: 1.16 g/cm³
Flash Point: 257.8 °C
Melting point: 54-57 °C
Storage temp.: 2-8 °C
Surface Tension: 45.2 dyne/cm
Enthalpy of Vaporization: 84.48 kJ/mol
Boiling Point: 502.6 °C at 760 mmHg
Vapour Pressure of L-Glutamic acid,N-[(1,1-dimethylethoxy)carbonyl]-, 5-cyclohexyl ester (CAS NO.73821-97-3): 1.82E-11 mmHg at 25 °C
Product Categories of L-Glutamic acid,N-[(1,1-dimethylethoxy)carbonyl]-, 5-cyclohexyl ester (CAS NO.73821-97-3): Amino Acid Derivatives; Amino Acids; Glutamic acid [Glu, E]; Boc-Amino Acids and Derivative
Canonical SMILES: CC(C)(C)OC(=O)NC(CCC(=O)OC1CCCCC1)C(=O)O
InChI: InChI=1S/C16H27NO6/c1-16(2,3)23-15(21)17-12(14(19)20)9-10-13(18)22-11-7-5-4-6-8-11/h11-12H,4-10H2,1-3H3,(H,17,21)(H,19,20)
InChIKey: FDNMLANBNJDIRG-UHFFFAOYSA-N

Boc-L-glutamic acid 5-cyclohexyl ester Safety Profile

WGK Germany: 3

Boc-L-glutamic acid 5-cyclohexyl ester Specification

L-Glutamic acid,N-[(1,1-dimethylethoxy)carbonyl]-, 5-cyclohexyl ester , its cas register number 73821-97-3. It also can be called Boc-Glu(Ochx)-OH ; Boc-L-glutamic acid 5-cyclohexyl ester ; and (2S)-5-(Cyclohexyloxy)-2-({[(2-methyl-2-propanyl)oxy]carbonyl}amino)-5-oxopentanoic acid .

Product Name

Boc-L-glutamic acid 5-cyclohexyl ester

Synthetic route

Boc-L-glutamic acid 5-cyclohexyl ester Chemical Properties

Boc-L-glutamic acid 5-cyclohexyl ester Safety Profile

Boc-L-glutamic acid 5-cyclohexyl ester Specification

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