5619-01-2

Basic information

• Product Name: Z-DL-GLU-OH
• Synonyms: CBZ-DL-GLU;LABOTEST-BB LT00441015;N-ALPHA-CARBOBENZOXY-DL-GLUTAMIC ACID;Z-DL-GLUTAMIC ACID;Z-DL-GLU-OH;Nsc169154
• CAS NO: 5619-01-2
• Molecular Formula: C₁₃H₁₅NO₆
• Molecular Weight: 281.26
• Mol File: 5619-01-2.mol

Chemical Properties

• Boiling Point: 529.1±50.0 °C(Predicted)
• Appearance: /
• Density: 1.360±0.06 g/cm3(Predicted)
• PKA: 3.81±0.10(Predicted)
• CAS DataBase Reference: Z-DL-GLU-OH(CAS DataBase Reference)
• NIST Chemistry Reference: Z-DL-GLU-OH(5619-01-2)
• EPA Substance Registry System: Z-DL-GLU-OH(5619-01-2)

Safety Data

• Hazardous Substances Data: 5619-01-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Z-DL-GLU-OH is used as a key intermediate in the synthesis of pomalidomide (P688200), a medication approved for the treatment of multiple myeloma, a type of cancer that affects plasma cells in the bone marrow. Its role in the synthesis process is crucial for the development of this therapeutic agent, which has demonstrated efficacy in treating patients with this condition.
Additionally, Z-DL-GLU-OH can be utilized in the synthesis of impurities related to pomalidomide, which is important for quality control and ensuring the safety and efficacy of the final drug product. By incorporating this building block into the synthesis of impurities, researchers can better understand their formation, properties, and potential impact on the overall drug quality.

Upstream product

• 204922-65-6 2-Benzyloxycarbonylamino-4-nitro-pentanedioic acid dimethyl ester 
• 204930-93-8 2-Benzyloxycarbonylamino-pentanedioic acid dimethyl ester 
• 19506-72-0 benzyl-8-quinolyl carbonate 
• 617-65-2 Glutamic acid 
• 501-53-1 benzyl chloroformate 

Downstream Products

• 110270-46-7 fluorure d'acide N carbobenzoxy DL-glutamique 
• 135263-61-5 diphenacyl benzyloxycarbonylglutamate 
• 393104-67-1 bis{2-[3,4-bis(undecyloxy)phenyl]ethyl} D,L-glutamate 
• 1155-62-0 N-benzyloxycarbonyl-L-glutamic acid 
• 95108-01-3 (4,8-Dioxo-3,9-dioxa-15-aza-bicyclo[9.3.1]pentadeca-1⁽¹⁴⁾,11⁽¹⁵⁾,12-trien-5-yl)-carbamic acid benzyl ester 
• 95107-91-8 (1,3-Bis-fluorocarbonyl-propyl)-carbamic acid benzyl ester 
• 125050-00-2 tert-butyl ester of D-glutamic acid semialdehyde oxime 
• 125050-16-0 N-(benzyloxy)amide of α-N-carbobenzoxy-δ-bromo-D-norvaline 
• 23577-92-6 γ-methyl-α-tert-butyl ester of N-carbobenzoxyglutamic acid 
• 125049-95-8 α-N-carbobenzoxy-δ-N-(benzyloxy)-D-cycloornithine 
• 5891-45-2 N-benzoyloxycarbonyl D-glutamic acid α-t-benzyl ester 
• 125050-18-2 tert-butyl ester of α-N-carbobenzoxy-δ-bromonorvaline 
• 125076-26-8 2-Benzyloxycarbonylamino-5-hydroxy-pentanoic acid tert-butyl ester 
• 125049-90-3 tert-butyl ester of α-N-carbobenzoxy-δ-N-(allyloxycarbonyl)-δ-N-(benzyloxy)-D-ornithine 

Relevant articles and documents

Total synthesis of (-)-platensimycin by advancing oxocarbenium- and iminium-mediated catalytic methods

(-)-Platensimycin is a potent inhibitor of fatty acid synthase that holds promise in the treatment of metabolic disorders (e.g., diabetes and "fatty liver") and pathogenic infections (e.g., those caused by drug-resistant bacteria). Herein, we describe its total synthesis through a four-step preparation of the aromatic amine fragment and an improved stereocontrolled assembly of the ketolide fragment, (-)-platensic acid. Key synthetic advances include 1) a modified Lieben haloform reaction to directly convert an aryl methyl ketone into its methyl ester within 30 seconds, 2) an experimentally improved dialkylation protocol to form platensic acid, 3) a sterically controlled chemo- and diastereoselective organocatalytic conjugate reduction of a spiro-cyclized cyclohexadienone by using the trifluoroacetic acid salt of α-amino di-tert-butyl malonate, 4) a tetrabutylammonium fluoride promoted spiro-alkylative para dearomatization of a free phenol to assemble the cagelike ketolide core with the moderate leaving-group ability of an early tosylate intermediate, and 5) a bismuth(III)-catalyzed Friedel-Crafts cyclization of a free lactol, with LiClO4 as an additive to liberate a more active oxocarbenium perchlorate species and suppress the Lewis basicity of the sulfonyloxy group. The longest linear sequence is 21 steps with an overall yield of 3.8% from commercially available eugenol. Relay tactics: The stereocontrolled assembly of the potent antibiotic (-)-platensimycin in 21 steps and 3.8% yield from eugenol is described (see scheme; TBAF: tetrabutylammonium fluoride; Ts: toluene-4-sulfonyl). Highlights are 1) a rapid oxidative esterification of an acyl aromatic, 2) a reliable dialkylation protocol to form platensic acid, 3) a π-facial conjugate reduction of a dienone, 4) a TBAF-promoted alkylative dearomatization of a free phenol, and 5) a Friedel-Crafts closure of a free lactol.

Beta-strand mimetics and method relating thereto

Conformationally constrained compounds which mimic the secondary structure of β-strand regions of biologically active peptides and proteins are disclosed. Such β-strand mimetic structures have utility over a wide range of fields, including use as diagnostic and therapeutic agents. Libraries containing the β-strand mimetic structures of this invention are also disclosed as well as methods for screening the same to identify biologically active members.

New synthetic routes to α-amino acids and γ-oxygenated α-amino acids. Reductive denitration and oxidative transformations of γ-nitro-α-amino acids

Transformation of γ-nitro-α-amino acid derivatives into α-amino acids by reductive denitration, into the γ-oxo-α-amino acids by ozonolysis of the corresponding amino acid ester nitronate derivatives, and into γ-hydroxy-α-amino acid derivatives by subsequent reduction of the oxo functionality, can be achieved in good yields. As the γ-nitro-α-amino acid derivatives are prepared from N,O-protected dehydroalanines derivable from the corresponding alanine, serine and cysteine derivatives by specific routes, the overall procedures provide a means for selective conversion of these simple α-amino acids into more complex ones.

Syntheses of Polypeptides by Hidrogenolysis of N-Benzyloxycarbonyl-Amino Acid Anhydrides

When anhydrides of N-benzyloxycarbonyl-DL-aspartic acid (Z-DL-Asp), Z-L-Asp, N-Z-DL-glutamic acid (Z-DL-Glu), Z-L-Glu and N-Z-3-aminoglutaric acid (Z-β-Agl) were hydrogenolyzed in N,N-dimethylformamide (DMF), polypeptides were obtained in high yields.Hydrogenolyses of Z-DL-Glu and Z-L-Glu in dioxane gave pyroglutamic acid.

Composition containing a penem or carbapenem antibiotic

Administration of an N-acylated amino acid in association with a penem or carbapenem antibiotic relieves or eliminates the renal problems associated with administration of the antibiotic alone. The amino acid derivative and antibiotic may be formulated together as a composition or administered separately, either simultaneously or sequentially. The composition may be prepared by simple mixing.