56877-41-9

Basic information

• Product Name: Z-GLU(OTBU)-OME
• Synonyms: N-ALPHA-CARBOBENZOXY-L-GLUTAMIC ACID-GAMMA-T-BUTYL ESTER-ALPHA-METHYL ESTER;Z-L-GLUTAMIC ACID GAMMA-T-BUTYL ESTER ALPHA-METHYL ESTER;Z-GLU(OTBU)-OME;Z-GLUTAMIC ACID METHYL ESTER;N-[(Phenylmethoxy)carbonyl]-L-glutamic acid 5-(1,1-dimethylethyl) 1-methyl ester;Z-L-Glu(OtBu)-OMe;Z-L-glutamic acid γ-tert-butyl ester α-methyl ester≥ 98% (HPLC)
• CAS NO: 56877-41-9
• Molecular Formula: C₁₈H₂₅NO₆
• Molecular Weight: 351.39
• Mol File: 56877-41-9.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• Storage Temp.: Store at 0°C
• CAS DataBase Reference: Z-GLU(OTBU)-OME(CAS DataBase Reference)
• NIST Chemistry Reference: Z-GLU(OTBU)-OME(56877-41-9)
• EPA Substance Registry System: Z-GLU(OTBU)-OME(56877-41-9)

Safety Data

• Hazardous Substances Data: 56877-41-9(Hazardous Substances Data)

Usage

Chemical Properties

Viscous liquid to white powder

Upstream product

• 67-56-1 methanol 
• 51644-83-8 N-(benzyloxy)carbonyl-D-glutamic acid 5-tert-butyl ester 
• 5672-83-3 Z-L-GluOMe 
• 115-11-7 isobutene 
• 4124-76-9 N-(benzyloxycarbonyl)-L-glutamic acid anhydride 
• 23632-68-0 4(S)-(2-tert-butoxycarbonylethyl)-5-oxo-oxazolidine 3-carboxylic acid benzyl ester 
• 3886-08-6 5-tert-butyl N-benzyloxycarbonyl-L-glutamate 
• 74-88-4 methyl iodide 
• 186581-53-3 diazomethane 

Downstream Products

• 53838-27-0 H-Glu(tBu)-OMe 
• 3886-08-6 5-tert-butyl N-benzyloxycarbonyl-L-glutamate 
• 17191-52-5 tert-butyl (4S)-5-amino-4-(benzyloxycarbonylamino)-5-oxo-pentanoate 
• 55592-89-7 N-Z-L-Glutaminsaeure-γ-tert.-butylester-α-hydrazid 
• 92506-78-0 4(S)-benzyloxycarbonylamino-5-oxo-pentanoic acid tert-butyl ester 
• 95716-10-2 Z-L-(glu)Thz-OH 
• 95716-09-9 Z-L-(glu)Thz-OMe 
• 92506-79-1 (R)-2-((S)-1-Benzyloxycarbonylamino-3-tert-butoxycarbonyl-propyl)-thiazolidine-4-carboxylic acid methyl ester 
• 95716-08-8 Z-L-(glu(OBu^t))Thz-OMe 
• 92506-82-6 Z-(gly)Thz-L-Pro-L-Leu-L-Val-L-(gln)Thz-OMe 
• 6234-04-4 N-Benzyloxycarbonyl-γ-tert.-butyl-L-glutamyl-L-alanin-hydrazid 
• 53665-73-9 N-Benzyloxycarbonyl-L-alanyl-γ-tert.-butyl-glutaminsaeuremethylester 
• 2419-56-9 L-glutamic acid 5-tert-butyl ester 
• 5249-68-3 N-benzyloxycarbonyl-γ-tert-butyl-L-glutamyl-L-alanine methyl ester 

Relevant articles and documents

Unusual orthogonality in the cleavage process of closely related chelating protecting groups for carboxylic acids by using different metal ions

Three structurally related relay protecting groups for carboxylic acids that are based on chelating amines have been developed. These protecting groups can easily be introduced by coupling the carboxylic acid and the corresponding amine in the presence of 2-(1Hbenzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (TBTU). In addition to being stable to a whole array of reaction conditions, these protecting groups are also stable under acidic and basic conditions, allowing them to be used in combination with the ester protection of carboxylic acids. The cleavage of these protecting groups is activated by the chelation of metal ions, involving an unusual coordination of the amide nitrogen. Despite their similarity, cleavage of these protecting groups is possible in both a stepwise and an orthogonal fashion by applying different metal salts.

Cleavage of benzyloxycarbonyl-5-oxazolidinones to α-benzyloxycarbonylamino-α-alkyl esters by alcohols and sodium hydrogen carbonate

The reaction of benzyloxycarbonyl-5-oxazolidinones with alcohols and sodium hydrogen carbonate to afford the corresponding benzyloxycarbonyl esters is described.

Methotrexate Analogues. 14. Synthesis of New γ-Substituted Derivatives as Dihydrofolate Reductase Inhibitors and Potential Anticancer Agents

The γ-tert-butyl ester (1), γ-hydrazide (2), γ-n-butylamide (3), and γ-benzylamide (4) derivatives of methotrexate (MTX) were synthesized from 4-amino-4-deoxy-N10-methylpteroic acid (APA) and the appropriate blocked L-glutamic acid precursors with the aid of the peptide bond forming reagent diethyl phosphorocyanidate.The affinity of these side chain modified products for dihydrofolate reductase (DHFR) from Lactobacillus casei and L1210 mouse leukemic cells was determined spectrophotometrically or by competitive radioligand binding assay, and their cytotoxicity was evaluated against L1210 leukemic cells in culture.The results provide continuing support for the view that the "γ-terminal region" of the MTX side chain is an attractive site for molecular modification of this anticancer agent.