35793-73-8

Basic information

• Product Name: Boc-D-Glutamic acid 5-benzyl ester
• Synonyms: BOC-GLUTAMIC ACID(OBZL)-OH;BOC-GLU(OBZL)-OH;BOC-L-GLUTAMIC ACID G-BENZYL ESTER;BOC-L-GLUTAMIC ACID (OBZL);BOC-L-GLUTAMIC ACID GAMMA-BENZYL ESTER;BOC-L-GLU(BZL)-OH;BOC-L-GLU(OBZL)-OH;T-BUTYLOXYCARBONYL-L-GLUTAMIC ACID GAMMA-BENZYL ESTER
• CAS NO: 35793-73-8
• Molecular Formula: C₁₇H₂₃NO₆
• Molecular Weight: 337.37
• EINECS: 237-007-5
• Product Categories: Amino Acid Derivatives
• Mol File: 35793-73-8.mol
• Article Data: 11

Chemical Properties

• Melting Point: 69-71 °C
• Boiling Point: 522.6 °C at 760 mmHg
• Flash Point: 269.9 °C
• Appearance: /
• Density: 1.197 g/cm³
• Vapor Pressure: 9.49E-12mmHg at 25°C
• Refractive Index: 1.523
• Storage Temp.: 2-8°C
• PKA: 3.81±0.10(Predicted)
• CAS DataBase Reference: Boc-D-Glutamic acid 5-benzyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Boc-D-Glutamic acid 5-benzyl ester(35793-73-8)
• EPA Substance Registry System: Boc-D-Glutamic acid 5-benzyl ester(35793-73-8)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 35793-73-8(Hazardous Substances Data)

Usage

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.

InChI:InChI=1/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

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 2578-33-8 D-glutamic acid-5-benzyl ester 
• 100-51-6 benzyl alcohol 
• 870-46-2 t-butoxycarbonylhydrazine 
• 6893-26-1 D-Glutamic acid 
• 1070-19-5 N-(tert-butyloxycarbonyl) azide 
• 16965-08-5 1,1-dimethylethyl 2,4,5-trichlorophenyl carbonate 
• 41840-28-2 S-tert-butoxycarbonyl-4,6-dimethyl-2-mercaptopyrimidine 

Downstream Products

• 117997-77-0 (R)-4-tert-Butoxycarbonylamino-4-dipentylcarbamoyl-butyric acid benzyl ester 
• 861819-80-9 benzyl N²-(tert-butoxycarbonyl)-N¹-(4-methylphenyl)-D-glutaminate 
• 63091-98-5 benzyl N²-(tert-butoxycarbonyl)-N¹-methyl-D-glutaminate 
• 110473-10-4 N-Boc-D-Glu α-methyl ester 
• 76379-00-5 N-tert-butoxycarbonyl-D-glutamic acid α-p-nitrophenyl-γ-benzyl ester 
• 123540-77-2 (R)-4-Dipentylcarbamoyl-4-[3-(3-methoxy-phenyl)-ureido]-butyric acid benzyl ester 
• 117997-78-1 (R)-4-Amino-4-dipentylcarbamoyl-butyric acid benzyl ester; hydrochloride 
• 123540-73-8 (R)-2-[3-(3-Methoxy-phenyl)-ureido]-5-oxo-5-pyrrolidin-1-yl-pentanoic acid dipentylamide 
• 117997-59-8 (R)-5-(dipropylamino)-4-<(1H-indol-2-ylcarbonyl)amino>-5-oxo-1-(phenylmethoxy)pentanoic acid 
• 116311-86-5 (R)-4-Dipentylcarbamoyl-4-[3-(3-methoxy-phenyl)-ureido]-butyric acid 
• 116311-84-3 (R)-5-(dipropylamino)-4-[(1H-indol-2-ylcarbonyl)amino]-5-oxo-pentanoic acid 
• 1205538-85-7 C₂₉H₄₄N₄O₇ 
• 117997-79-2 (R)-4-Amino-4-dicyclohexylcarbamoyl-butyric acid benzyl ester; hydrochloride 
• 1286246-27-2 Nα-[4-chlorocinnamoyl-L-alanyl-D-isoglutaminyl]-L-lysine 

Relevant articles and documents

Synthesis of Carbapenems Containing Peptidoglycan Mimetics and Inhibition of the Cross-Linking Activity of a Transpeptidase of l,d Specificity

The carbapenem class of β-lactams has been optimized against Gram-negative bacteria producing extended-spectrum β-lactamases by introducing substituents at position C2. Carbapenems are currently investigated for the treatment of tuberculosis as these drugs are potent covalent inhibitors of l,d-transpeptidases involved in mycobacterial cell wall assembly. The optimization of carbapenems for inactivation of these unusual targets is sought herein by exploiting the nucleophilicity of the C8 hydroxyl group to introduce chemical diversity. As β-lactams are structure analogs of peptidoglycan precursors, the substituents were chosen to increase similarity between the drug and the substrate. Fourteen peptido-carbapenems were efficiently synthesized. They were more effective than the reference drug, meropenem, owing to the positive impact of a phenethylthio substituent introduced at position C2 but the peptidomimetics added at position C8 did not further improve the activity. Thus, position C8 can be modified to modulate the pharmacokinetic properties of highly efficient carbapenems.

Preparation method of dexloxiglumide

The invention discloses a preparation method of dexloxiglumide. The preparation method comprises the following steps: carrying out an acylation reaction on N-boc-D-glutamic acid-5-benzyl ester with N-(3-methoxypropyl)-amylamine by a mixed anhydride method, then removing boc groups to obtain the following compound, then carrying out a reaction on the obtained compound with 3,4-dichlorobenzoyl chloride to generate the following compound, and finally removing benzyl groups to obtain dexloxiglumide. Compared with the prior art, the method provided by the invention is simpler in operation and is more efficient.

CHEMICAL SYNTHESIS AND ANTI-TUMOR AND ANTI-METASTATIC EFFECTS OF DUAL FUNCTIONAL CONJUGATE

The present invention discloses chemical synthesis, anti-tumor and anti-metastatic effects of a dual functional conjugate as showed by formula I. In detail, paclitaxel or docetaxol is linked with muramyl dipeptide derivative to form a conjugate, thus dual anti-tumor and anti-metastatic effects are achieved by combination of chemotherapy and immunotherapy. The present invention also discloses that paclitaxel or docetaxol and muramyl dipeptide derivative conjugate is synthesized by combination of solid-phase and solution-phase synthesis, and said conjugate can be used in manufacture of anti-tumor medicaments as proved by reliable bioassays.