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

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

Used in Pharmaceutical Industry:
Boc-D-Glutamic acid 5-benzyl ester is used as an amino acid building block for the synthesis of peptides. Its application is crucial in the pharmaceutical industry due to the growing market for peptide drugs. The fast and reliable synthesis of peptides is of great importance for the development of new therapeutic agents and medicines.
Used in Peptide Drug Development:
Boc-D-Glutamic acid 5-benzyl ester is utilized as a key component in the creation of peptide drugs. Its unique structure allows for the formation of specific peptide sequences that can target various biological processes and pathways. This makes it a valuable tool in the design and synthesis of novel peptide-based therapeutics.
Used in Research and Development:
In the field of research and development, Boc-D-Glutamic acid 5-benzyl ester serves as an important compound for studying the properties and functions of peptides. Its use in peptide synthesis allows scientists to explore the potential of these biomolecules in various applications, such as drug discovery, diagnostics, and therapeutics.
Overall, Boc-D-Glutamic acid 5-benzyl ester is a vital amino acid derivative that plays a significant role in the synthesis and development of peptide-based drugs and therapeutics. Its applications in the pharmaceutical industry, peptide drug development, and research and development highlight its importance in the field of biotechnology and medicine.

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

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

Downstream Products

• 117997-80-5 N^α-Boc-ε-benzyl-D-glutamic acid dipropylamide 
• 117997-77-0 (R)-4-tert-Butoxycarbonylamino-4-dipentylcarbamoyl-butyric acid benzyl ester 
• 263247-61-6 (R)-N-(4-pentenyl)-N-pentyl γ-benzyl-N_α-t-butoxycarbonylglutamic acid amide 
• 110473-10-4 N-Boc-D-Glu α-methyl ester 
• 945493-35-6 (R)-2-(N-Boc-amino)-5-(triisopropylsilyloxy)pentan-1-ol 
• 945493-36-7 (R)-N¹-allyl-N²-Boc-N¹-(o-nitrobenzenesulfonyl)-5-(triisopropylsilyloxy)pentane-1,2-diamine 
• 945493-34-5 C₂₃H₄₁N₃O₅SSi 
• 945492-94-4 (2R,S)-2-[N-allyl-3-(4-benzyloxyphenyl)propanamido]-N-[(2R)-1-(N-allyl-o-nitrophenylsulfonamido)-5-triisopropylsilyloxypentan-2-yl]-5-triisopropylsilyloxypentanamide 
• 945492-98-8 (2R)-2-[N-allyl-3-(4-benzyloxyphenyl)acetamido]-N-[(2R)-1-(N-allyl-o-nitrophenylsulfonamido)-5-triisopropylsilyloxypentan-2-yl]-5-triisopropylsilyloxypentanamide 
• 945492-97-7 (2S)-2-[N-allyl-3-(4-benzyloxyphenyl)acetamido]-N-[(2R)-1-(N-allyl-o-nitrophenylsulfonamido)-5-triisopropylsilyloxypentan-2-yl]-5-triisopropylsilyloxypentanamide 
• 945493-02-7 (2R,5R,6E)-2,5-bis[3-(triisopropylsilyloxy)propyl]-1-[3-(4-benzyloxyphenyl)propionyl]-7-(o-nitrobenzenesulfonyl)-1,4,7-triazacycloundec-9-en-3-one 
• 945493-01-6 (2S,5R,6E)-2,5-bis[3-(triisopropylsilyloxy)propyl]-1-[3-(4-benzyloxyphenyl)propionyl]-7-(o-nitrobenzenesulfonyl)-1,4,7-triazacycloundec-9-en-3-one 
• 945493-06-1 (2R,5R,6E)-2,5-bis[3-(triisopropylsilyloxy)propyl]-1-(4-benzyloxyphenylacetyl)-7-(o-nitrobenzenesulfonyl)-1,4,7-triazacycloundec-9-en-3-one 
• 945493-05-0 (2S,5R,6E)-2,5-bis[3-(triisopropylsilyloxy)propyl]-1-(4-benzyloxyphenylacetyl)-7-(o-nitrobenzenesulfonyl)-1,4,7-triazacycloundec-9-en-3-one 

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.

NOVEL MURAMYL PEPTIDE DERIVATIVE COMPOUND, SYNTHESIS AND USES THEREOF

The invention relates to novel Muramyl Dipeptide (MDP) derivative compound of structural Formula-VIII, a process for synthesis, intermediates used in the synthesis and use thereof; wherein R1 and R2 both are hydrogen; or R1 is hydrogen and R2 is alkyl or aryl; or R1 is alkyl or aryl and R2 is hydrogen; or R1 and R2 both are alkyl or aryl (same or different groups); wherein alkyl group constitute C1-C6 alkyl or higher (both linear and branched) with or without heteroatoms; and aryl group constitute phenyl, substituted phenyl, heteraryl, arylalkyl and polynuclear aromatics. These compounds possess excellent pharmacological properties, in particular immunomodulating properties for use as adjuvant in vaccine formulations. These compounds are, particularly useful as adjuvants in vaccines.

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.

NOVEL MURAMYL PEPTIDE DERIVATIVE COMPOUND, SYNTHESIS AND USES THEREOF

The invention relates to novel Muramyl Dipeptide (MDP) derivative compound of structural Formula-VIII, a process for synthesis, intermediates used in the synthesis and use thereof. R = alkyl (both linear and branched), aryl, substituted aryl, alkoxy alkyl Wherein, R can be both linear and branched alkyl, aryl, substituted aryl and alkoxy alkyl. These compounds possess excellent pharmacological properties, in particular immunomodulating properties for use as adjuvant in vaccine formulations. These compounds are, particularly useful as adjuvants in vaccines.

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.

Solution-phase synthesis of a muramyl dipeptide analogue MDA

The solution-phase synthesis of a muramyl dipeptide (MDP) analogue of Nα-[4-chlorocinnamoyl-l-alanyl-d-isoglutaminyl]-l-lysine (MDA, 2) is reported that possesses the features of easy feasibility, safety and low cost in large scale of synthesis.

Design and synthesis of all diastereomers of cyclic pseudo-dipeptides as mimics of cyclic CXCR4 pentapeptide antagonists

The four diastereomers of 2,5-bis[(3-guanidino)propyl]-1-[3-(4- hydroxyphenyl)propionyl]-7-(2-naphthylacetyl)-1,4,7-triazacycloundec-9-en-3-one (54-57) and of 2,5-bis[(3-guanidino)propyl]-1-(4-hydroxyphenylacetyl)-7-(2- naphthylacetyl)-1,4,7-triazacycloundec-9-en-3-one (58-61) were synthesized by a divergent methodology from l- and d-glutamic acids. The 11-membered ring core was made by ring closing metathesis of linear bis(allylamines), and the guanidyl functions were introduced by a simultaneous double Mitsunobu reaction using bis(Boc)guanidine. These compounds were designed to mimic cyclic pentapeptide FC131 (c[Gly-d-Tyr-Arg-Arg-Nal]). The Royal Society of Chemistry.

Solid-phase synthesis of muramyl dipeptide (MDP) derivatives using a multipin method

Solid-phase synthetic method of muramyl dipeptide derivatives is reported. A diverse library of muramyl dipeptides could be potentially synthesized by acylation, reductive alkylation, sulfonamide formation, urea formation, N-alkylation, amine addition, or component Ugi reactions based on this method for drug screening. (C) 2000 Elsevier Science Ltd. All rights reserved.

Synthesis of a radoilabeled type A cholecystokinin receptor antagonist, (R)-N-pentyl-N-(4,5-di[3H]pentyl)N(α)-(3-quinolinoyl)glutamic acid amide

A method for the preparation of a radiolabeled CCK(A)-specific antagonist, (R)-N-pentyl-N-(4,5-di[3H]pentyl)N(α)-(3-quinolinoyl)glutamic acid amide, [3H]-A-65186, is described. (R)-γ-Benzyl-N-BOC-glutamic acid was coupled with N-(4-pentenyl)-N-pentylamine using BOPCl and TEA in dichloromethane to provide the corresponding amide. Deprotection of the α-amino moiety followed by coupling with 3-quinolinecarboxylic acid in the presence of EDCI, TEA, and HOBt in dichloromethane resulted in (R)-N-(4-pentenyl)-N-pentyl γ-benzyl-N(α)-(3-quinolinoyl)glutamic acid amide. Tritiation with concomitant hydrogenolysis of the benzyl ester proceeds smoothly to provide [3H]-A-65186.