471242-80-5

Basic information

• Product Name: Dimethyl Hydroxyaspartate, Mixture of Diastereomers
• Synonyms: Dimethyl Hydroxyaspartate, Mixture of Diastereomers;3-Hydroxy-aspartic Acid DiMethyl Ester
• CAS NO: 471242-80-5
• Molecular Formula: C6H11NO5
• Molecular Weight: 177.15524
• Product Categories: Amino Acids & Derivatives
• Mol File: 471242-80-5.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• Solubility: Ethyl Acetate, Methanol
• CAS DataBase Reference: Dimethyl Hydroxyaspartate, Mixture of Diastereomers(CAS DataBase Reference)
• NIST Chemistry Reference: Dimethyl Hydroxyaspartate, Mixture of Diastereomers(471242-80-5)
• EPA Substance Registry System: Dimethyl Hydroxyaspartate, Mixture of Diastereomers(471242-80-5)

Safety Data

• Hazardous Substances Data: 471242-80-5(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

Dimethyl Hydroxyaspartate, Mixture of Diastereomers (cas# 471242-80-5) is a compound useful in organic synthesis.

Upstream product

• 109874-90-0 dimethyl (2S,3R)-2-bromo-3-hydroxysuccinate 
• 117470-90-3 (4R,5R)-2,2-Dioxo-2λ⁶-[1,3,2]dioxathiolane-4,5-dicarboxylic acid dimethyl ester 
• 67-56-1 methanol 
• 1186-90-9 erythro-β-hydroxy-DL-aspartic acid 
• 4294-45-5 DL-threo-β-hydroxyaspartic acid 

Downstream Products

• 471242-81-6 (DL-threo)-dimethyl 2-[(tert-butoxycarbonyl)amino]-3-hydroxysuccinate 
• 84107-20-0 (L-threo)-dimethyl 2-[(tert-butoxycarbonyl)amino]-3-hydroxy succinate 

Relevant articles and documents

β-Indolyloxy Functionalized Aspartate Analogs as Inhibitors of the Excitatory Amino Acid Transporters (EAATs)

The excitatory amino acid transporters (EAATs) mediate uptake of the major excitatory neurotransmitter l-glutamate (Glu). The essential functions governed by these transporters in regulating the central Glu level make them interesting therapeutic targets in a wide range of neurodegenerative and psychiatric disorders. l-Aspartate (Asp), another EAAT substrate, has served as a privileged scaffold for the development of EAAT inhibitors. In this study, we designed and synthesized the first β-indolyloxy Asp analogs 15a-d with the aim to probe a hitherto unexplored adjacent pocket to the substrate binding site. The pharmacological properties of 15a-d were characterized at hEAAT1-3 and rEAAT4 in a conventional [3H]-d-Asp uptake assay. Notably, thiophene analog 15b and the para-Trifluoromethyl phenyl analog 15d were found to be hEAAT1,2-preferring inhibitors exhibiting IC50values in the high nanomolar range (0.21-0.71 μM) at these two transporters versus IC50values in the low micromolar range at EAAT3,4 (1.6-8.9 μM). In summary, the results presented herein open up for further structure-Activity relationship studies of this new scaffold.

Synthesis of a protected derivative of (2R,3R)-β-hydroxyaspartic acid suitable for Fmoc-based solid phase synthesis

Synthesis of d-threo-hydroxyaspartic acid, orthogonally protected and compatible with an Fmoc solid-phase peptide synthesis strategy is reported. This synthetic procedure starting from (2R,3R)-dimethyltartrate is adaptable to a multi-gram scale. 2,2-Dimethyl-5-oxo-1,3-dioxazolane formation between the β-hydroxy alcohol and the β-carboxylic functions constitutes a key step of the differentiation of the two acidic functions allowing the preparation of (2R,3R)-Fmoc-β-hydroxyaspartic α-allyl ester.