109874-90-0

Upstream product

• 608-68-4 dimethyl L-tartrate 
• 78816-00-9 dimethyl (2R)-acetoxy-(3S)-bromosuccinate 
• 72229-27-7 dimethyl (R,R)-O-acetyl-tartrate 
• 117470-90-3 (4R,5R)-2,2-Dioxo-2λ⁶-[1,3,2]dioxathiolane-4,5-dicarboxylic acid dimethyl ester 

Downstream Products

• 57302-79-1 (3-hydroxymethyl-oxiranyl)-methanol 
• 471242-80-5 2-amino-3-hydroxy-succinic acid dimethyl ester 

Relevant academic research and scientific papers

NOVEL APPROACH TO STEREOISOMERICALLY FULL SET OF OPTICALLY PURE 2,3-EPOXYESTERS FROM TARTARIC ACIDS

Four possible stereoisomers of 4-(t-butyldimethylsilyloxy)-2,3-epoxybutanoic acid esters have been synthesized highly efficiently in both diastereomerically and enantiomericaly pure state from tartaric acids.

Effect of electron-withdrawing substituents on the epoxide ring: An experimental and theoretical electron density analysis of a series of epoxide derivatives

A series of acceptor-substituted epoxide derivatives is scrutinized by means of experimental and theoretical electron-density investigations. Due to the possibility of nucleophilic ring-opening, the epoxide ring is not only a very useful functional group in organic synthesis, but acceptor-substituted epoxides are valuable building blocks for the design of protease inhibitors. Therefore, the electron-density analysis in this work focuses on two main aspects that can contribute to rational drug design: (i) the quantification of the electron-withdrawing substituent effects on the epoxide ring and (ii) the intermolecular interactions involving the epoxide ring in combination with different substituents. It can be shown that the electron-withdrawing properties of the substituents cause an elongation of the C-C bonds in the epoxide rings and the loss of electron density can be measured by an analysis of critical points, atomic charges, and the source function. The different strengths of the substituents are reflected in these properties. Covalent and electrostatic contributions to the intermolecular interactions and thus the lattice energies are depicted on different molecular surfaces.(Figure Presented)

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.

A revised mechanism for chemoselective reduction of esters with borane-dimethyl sulfide complex and catalytic sodium tetrahydroborate directed by adjacent hydroxyl group

The plausible mechanism for the reduction of the ester groups with a strong preference for one located α to the hydroxyl groups of (S)-malates and (R,R)-tartrate-based derivatives has been proposed together with some results with regard to its applications to the syntheses of chiral synthons.