| Identification | More | [Name]
Boc-D-Glutamic acid 5-benzyl ester | [CAS]
35793-73-8 | [Synonyms]
5-BENZYL N-BOC-L-GLUTAMATE
5-BENZYL N-(TERT-BUTOXYCARBONYL)-L-GLUTAMATE
BOC-GLU(OBZL)
BOC-GLU(OBZL)-OH
BOC-GLUTAMIC ACID(OBZL)-OH
BOC-L-GLU(BZL)-OH
BOC-L-GLU(OBZL)-OH
BOC-L-GLUTAMIC ACID 5-BENZYL ESTER
BOC-L-GLUTAMIC ACID GAMMA-BENZYL ESTER
BOC-L-GLUTAMIC ACID G-BENZYL ESTER
BOC-L-GLUTAMIC ACID (OBZL)
N-ALPHA-T-BOC-L-GLUTAMIC ACID GAMMA-BENZYL ESTER
N-ALPHA-T-BUTOXYCARBONYL-L-GLUTAMIC ACID GAMMA-BENZYL ESTER
N-ALPHA-TERT-BOC-L-GLUTAMIC-GAMMA-BENZYL ESTER
N-ALPHA-TERT-BUTYLOXYCARBONYL-L-GLUTAMIC ACID GAMMA-BENZYL ESTER
N-BOC-L-GLUTAMIC ACID 5-BENZYL ESTER
N-T-BOC-L-GLUTAMIC ACID GAMMA-BENZYL ESTER
N-T-BUTOXYCARBONYL-L-GLUTAMIC ACID 5-BENZYL ESTER
N-(TERT-BUTOXYCARBONYL)-L-GLUTAMIC ACID 5-BENZYL ESTER
TBOC-L-GLUTAMIC ACID (OBZL) | [EINECS(EC#)]
237-007-5 | [Molecular Formula]
C17H23NO6 | [MDL Number]
MFCD00065569 | [Molecular Weight]
337.37 | [MOL File]
35793-73-8.mol |
| Chemical Properties | Back Directory | [Melting point ]
69-71 °C | [alpha ]
5.5 º (c=1% in acetic acid) | [Boiling point ]
522.6±50.0 °C(Predicted) | [density ]
1?+-.0.06 g/cm3(Predicted) | [storage temp. ]
2-8°C
| [form ]
solid | [pka]
3.81±0.10(Predicted) | [color ]
White | [Major Application]
peptide synthesis | [InChI]
1S/C17H23NO6/c1-17(2,3)24-16(22)18-13(15(20)21)9-10-14(19)23-11-12-7-5-4-6-8-12/h4-8,13H,9-11H2,1-3H3,(H,18,22)(H,20,21)/t13-/m1/s1 | [InChIKey]
AJDUMMXHVCMISJ-CYBMUJFWSA-N | [SMILES]
N([C@H](CCC(=O)OCc1ccccc1)C(=O)O)C(=O)OC(C)(C)C | [CAS DataBase Reference]
35793-73-8(CAS DataBase Reference) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H315-H319-H335 | [Precautionary statements ]
P280-P271 | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
3
| [HS Code ]
2922500090 | [Storage Class]
11 - Combustible Solids |
| Hazard Information | Back Directory | [Uses]
Boc-Glu(OBzl)-OH, is an amino acid building block used in peptide synthesis. With a growing peptide drug market the fast, reliable synthesis of peptides is of great importance. | [reaction suitability]
reaction type: Boc solid-phase peptide synthesis | [Synthesis]
(R)-2-Amino-5-(benzyloxy)-5-oxovaleric acid (6.0 g, 25.3 mmol) was used as a starting material, which was dissolved in a mixed solvent of dioxane and water (1:1, 40 mL). To this solution was added di-tert-butyl dicarbonate (Boc2O, 6.62 g, 30.36 mmol) at 0 °C. The reaction mixture was stirred at room temperature for 16 hours. After completion of the reaction, the solvent was removed by distillation under reduced pressure. The residue was diluted with 30 mL of water and alkalized with sodium carbonate (Na2CO3). Subsequently, the aqueous layer was washed with ethyl acetate (EtOAc, 3 x 100 mL). The aqueous layer was adjusted to pH 2-3 with 5 M HCl aqueous solution and then extracted with ethyl acetate (EtOAc, 4 × 100 mL). The organic extracts were combined, washed with brine and dried with anhydrous sodium sulfate (Na2SO4). Finally, the solvent was removed by distillation under reduced pressure to afford the target product (R)-5-(benzyloxy)-2-((tert-butoxycarbonyl)amino)-5-oxopentanoic acid [Compound 3j, 8.19 g, 96% yield] as a viscous, colorless oil. The product was structurally confirmed by nuclear magnetic resonance hydrogen spectroscopy (1H NMR, CDCl3) and electrospray mass spectrometry (ESI MS). | [References]
[1] Patent: WO2017/98529, 2017, A1. Location in patent: Page/Page column 18; 32
[2] Patent: EP2612857, 2017, B1. Location in patent: Paragraph 0123-0124
[3] Organic and Biomolecular Chemistry, 2007, vol. 5, # 12, p. 1915 - 1923
[4] Chinese Chemical Letters, 2011, vol. 22, # 12, p. 1443 - 1446 |
|
| Company Name: |
Alfa Aesar
|
| Telephone: |
400-6106006 |
| Website: |
http://chemicals.thermofisher.cn |
| Company Name: |
Jia Xing Isenchem Co.,Ltd
|
| Telephone: |
0573-85285100 18627885956 |
| Website: |
https://www.chemicalbook.com/ShowSupplierProductsList14265/0_EN.htm |
|