DL-TBOA

Base Information

• Chemical Name: DL-TBOA
• CAS No.: 205309-81-5
• Molecular Formula: C11H13NO5
• Molecular Weight: 239.22500
• Mol file: 205309-81-5.mol

Synonyms:rel-(3R)-3-(Phenylmethoxy)-D-aspartic acid;DL-threo-β-Benzyloxyaspartate;D-Aspartic acid, 3-(phenylmethoxy)-, (3R)-rel-;

Chemical Property of DL-TBOA

Chemical Property:

• PSA: 109.85000
• LogP: 0.76860
• Storage Temp.: Desiccate at -20°C
• Solubility.: <23.92mg/ml in DMSO;insoluble in H2O

Purity/Quality:

97% ^*data from raw suppliers

DL-TBOA ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Description: DL-TBOA is an inhibitor of excitatory amino acid transporters (EAATs), with IC50 values of 67 and 5.5 μM for glutamate uptake in COS-1 cells expressing human EAAT1 and EAAT2, respectively. It inhibits inward currents induced by L-aspartate in EAAT4-expressing Xenopus oocytes (Ki = 4.4 μM) and by L-glutamate in EAAT5-expressing oocytes (Ki = 3.2 μM) voltage-clamped at -60 mV. In vivo, DL-TBOA (500 μM, intrahippocampal perfusion) increases extracellular aspartate, glutamate, and alanine levels in rat hippocampus. Intrahippocampal injection of DL-TBOA increases lesion volume in the rat CA1 region in a dose-dependent manner and induces hyperexcitability, wet-dog shakes, salivation, forelimb myoclonus, limbic seizures, and epileptic EEG discharges at a dose of 25 nmol. DL-TBOA (5 and 10 μg, intrathecal) induces antinociception in the second phase of the formalin test in rats when administered 10 minutes prior to formalin.
• Uses: DL-TBOA is a non-transportable excitatory amino acid transporter (EAAT) inhibitor (1). DL-TBOA is a glutamate uptake inhibitor.

Technology Process of DL-TBOA

There total 35 articles about DL-TBOA which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 78.0%

C11H10O5 → L-threo-β-oxybenzylaspartic acid (205309-81-5)

Guidance literature:

With methylaspartate ammonia lyase L₃₈₄G mutant; ammonium chloride; magnesium chloride; at 20 ℃; for 24h; pH=9; Reagent/catalyst; stereoselective reaction; Kinetics; Catalytic behavior; Enzymatic reaction;

DOI:10.1002/cctc.201500318

Reference yield:

4-(1-benzyloxy-2-oxo-ethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester → D-erythro-β-benzyloxyaspartate (205309-81-5)

Guidance literature:

Multi-step reaction with 6 steps

1: Jones reagent

3: H⁺ / methanol

4: Jones reagent

5: NaOH

6: TFA

With sodium hydroxide; jones reagent; hydrogen cation; trifluoroacetic acid; In methanol; 1: Oxidation / 2: Methylation / 3: acidolysis / 4: Oxidation / 5: Hydrolysis / 6: acidolysis;

DOI:10.1016/S0960-894X(00)00487-X

Reference yield:

4-(1-benzyloxy-2-oxo-ethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester → L-erythro-β-benzyloxyaspartate (205309-81-5)

Guidance literature:

Multi-step reaction with 6 steps

1: Jones reagent

3: H⁺ / methanol

4: Jones reagent

5: NaOH

6: TFA

With sodium hydroxide; jones reagent; hydrogen cation; trifluoroacetic acid; In methanol; 1: Oxidation / 2: Methylation / 3: acidolysis / 4: Oxidation / 5: Hydrolysis / 6: acidolysis;

DOI:10.1016/S0960-894X(00)00487-X

upstream raw materials:

(2S,3S)-2-Amino-3-benzyloxy-succinic acid 1-(7-methoxy-2-oxo-2H-chromen-4-ylmethyl) ester

(2S,3S)-2-Amino-3-benzyloxy-succinic acid 1-(7-carboxymethoxy-2-oxo-2H-chromen-4-ylmethyl) ester

4-(1-benzyloxy-allyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

(2S,3R)-2-Benzyloxy-3-tert-butoxycarbonylamino-4-hydroxy-butyric acid methyl ester