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

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 
• 186581-53-3 diazomethane 
• 3886-08-6 5-tert-butyl N-benzyloxycarbonyl-L-glutamate 
• 74-88-4 methyl iodide 
• 23632-68-0 4(S)-(2-tert-butoxycarbonylethyl)-5-oxo-oxazolidine 3-carboxylic acid benzyl ester 
• 4124-76-9 N-(benzyloxycarbonyl)-L-glutamic acid anhydride 

Downstream Products

• 5672-83-3 Z-L-GluOMe 
• 26566-11-0 N-(benzyloxycarbonyl)-D-glutamic acid 1-methyl ester 
• 6233-91-6 N-Benzyloxycarbonyl-γ-tert.-butyl-L-glutaminsaeure-pentachlor-phenyl-diester 
• 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 
• 106930-52-3 S-4-benzyloxycarbonylamino-5-hydroxy-pentanoic acid tert-butyl ester 
• 344765-07-7 2-(4-methoxy-benzylamino)-pentanedioic acid 5-tert-butyl ester 1-methyl ester 
• 489432-92-0 (E)-But-2-enoic acid ((S)-2-hydroxy-tetrahydro-pyran-3-yl)-(4-methoxy-benzyl)-amide 
• 489432-91-9 (S)-2-[((E)-But-2-enoyl)-(4-methoxy-benzyl)-amino]-5-hydroxy-pentanoic acid methyl ester 
• 489432-90-8 (S)-2-[((E)-But-2-enoyl)-(4-methoxy-benzyl)-amino]-pentanedioic acid 5-tert-butyl ester 1-methyl ester 
• 115553-99-6 2(S),3'(S)-1-(3-amino-3-carboxypropyl)-5-oxo-2-pyrrolidinecarboxylic acid 
• 79640-76-9 γ-tert-butyl N-(4-amino-4-deoxy-N¹⁰-methylpteroyl)-L-glutamate 

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.

Synthesis of carbosilane dendritic wedges and their use for the construction of dendritic receptors

A divergent route for the synthesis of carbosilane wedges that contain either a bromine or amine as focal point has been developed. These new building blocks enable the construction of various core-functionalized carbosilane dendrimers. As a typical example carbosilane dendrimers up to the third generation containing a N,N′,N″-1,3,5-benzenetricarboxamide core (G1-G3) have been synthesized. This new class of molecules has been studied as host molecules and they have been found to bind protected amino acids as guest molecules via hydrogen bonding interactions. A decrease in the association constants was observed for the higher generation dendritic hosts, which is attributed to the increased steric hindrance around the core where the binding site is located. The binding properties of the dendritic host molecules can be tuned by modifying the binding motif at the core of the carbosilane dendrimers. A higher association constant for N-CBZ-protected glutamic acid 1-methyl ester (5) was observed when the third generation N,N′,N″-1,3,5-tris(l- alaninyl)benzenetricarboxamide core-functionalized carbosilane dendrimer (G3′) was used as the host molecule compared to G3. Different association constants for the formation of the diastereomeric G3′·l-5 (K = 295 M-1) and G3′·d-5 (K = 236 M-1) host-guest complexes were observed, pointing to a small enantioselective recognition effect. The difference between the association constants for the formation of the G3′·(l-5)2 and G3′·(d-5)2 host-guest complexes was much more pronounced, K = 37 M-1 versus K = 10 M-1, respectively. The Royal Society of Chemistry 2006.

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.

A New Acidic Amino Acid from a Basidiomycetes, Lactarius piperatus

A new acidic amino acid was isolated from a Basidiomycetes, Lactarius piperatus (Fr.) S.F.GRAY.The structure of this compound has been determined as 2(S),3'(S)-1-(3-amino-3-carboxypropyl)-5-oxo-2-pyrrolidinecarboxylic acid (1) on the basis of nuclear magn

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.