18289-89-9

Usage

Uses

Used in Pharmaceutical Industry:
(R)-Methyl 2,3-dihydroxypropanoate is used as a starting material or intermediate for the synthesis of various pharmaceuticals. Its chiral nature allows for the production of enantiomerically pure compounds, which are essential in the development of effective and safe medications.
Used in Agrochemical Industry:
(R)-Methyl 2,3-dihydroxypropanoate is used as a key intermediate in the synthesis of agrochemicals, such as pesticides and herbicides. Its ability to be incorporated into chiral molecules contributes to the development of more targeted and environmentally friendly agrochemicals.
Used in Fine Chemicals Industry:
(R)-Methyl 2,3-dihydroxypropanoate is utilized as a versatile building block in the synthesis of fine chemicals, including fragrances, flavors, and other specialty chemicals. Its unique properties enable the creation of high-quality and innovative products in this industry.
Used in Chiral Synthesis:
(R)-Methyl 2,3-dihydroxypropanoate is used as a chiral building block in organic synthesis, particularly for the production of chiral drugs and drug intermediates. Its stereochemistry plays a crucial role in the development of enantiomerically pure compounds, which are essential for the pharmaceutical industry.

Upstream product

• 67-56-1 methanol 
• 473-81-4 glyceric acid 
• 473-81-4 D-glyceric acid 
• 52373-72-5 methyl (R)-2,2-dimethyl-1,3-dioxolane-4-carboxylate 
• 312-84-5 D-Serine 
• 292638-85-8 acrylic acid methyl ester 
• 4538-50-5 methyl glycidate 
• 57-48-7 D-Fructose 
• 149-73-5 trimethyl orthoformate 

Downstream Products

• 16814-88-3 methyl (2R)-2-methoxy-3-(triphenylmethoxy)propanoate 
• 55032-29-6 (R)-2-(4-vinyl-phenyl)-[1,3,2]dioxaborolane-4-carboxylic acid methyl ester 
• 52373-72-5 methyl (R)-2,2-dimethyl-1,3-dioxolane-4-carboxylate 
• 132446-38-9 3-O-dimethoxytrityl-(R)-glyceric acid methyl ester 
• 14028-62-7 D-glyceric acid, calcium salt 
• 142564-20-3 (-)-methyl-(2R)-3-(tert-butyldiphenylsilyloxy)-2-hyrdoxypropanoate 
• 212051-35-9 (R)-methyl 3-((4-methoxybenzyl)oxy)-2-methylpropanoate 
• 212051-39-3 methyl 3-(3,4-dimethoxy-benzyloxy)-2-(R)-methyl-propionate 
• 873936-25-5 (2S,4R)-((Z)-2-Heptadec-8-enyl)-[1,3]dioxolane-4-carboxylic acid methyl ester 
• 873936-26-6 (2R,4R)-((Z)-2-Heptadec-8-enyl)-[1,3]dioxolane-4-carboxylic acid methyl ester 
• 209907-54-0 methyl (2R)-3-benzyloxy-2-hydroxypropanoate 
• 100-51-6 benzyl alcohol 
• 140-11-4 Benzyl acetate 
• 77522-15-7 (2R)-2,3-dihydroxy-3-methylbutan-1-yl p-toluenesulfonate 

Relevant academic research and scientific papers

Aromatic Donor-Acceptor Interaction-Based Co(III)-salen Self-Assemblies and Their Applications in Asymmetric Ring Opening of Epoxides

Aromatic donor-acceptor interaction as the driving force to assemble cooperative catalysts is described. Pyrene/naphthalenediimide functionalized Co(III)-salen complexes self-assembled into bimetallic catalysts through aromatic donor-acceptor interactions and showed high catalytic activity and selectivity in the asymmetric ring opening of various epoxides. Control experiments, nuclear magnetic resonance (NMR) spectroscopy titrations, mass spectrometry measurement, and X-ray crystal structure analysis confirmed that the catalysts assembled based on the aromatic donor-acceptor interaction, which can be a valuable noncovalent interaction in supramolecular catalyst development.

An Esterase-like Lyase Catalyzes Acetate Elimination in Spirotetronate/Spirotetramate Biosynthesis

Spirotetronate and spirotetramate natural products include a multitude of compounds with potent antimicrobial and antitumor activities. Their biosynthesis incorporates many unusual biocatalytic steps, including regio- and stereo-specific modifications, cyclizations promoted by Diels–Alderases, and acetylation-elimination reactions. Here we focus on the acetate elimination catalyzed by AbyA5, implicated in the formation of the key Diels–Alder substrate to give the spirocyclic system of the antibiotic abyssomicin C. Using synthetic substrate analogues, it is shown that AbyA5 catalyzes stereospecific acetate elimination, establishing the (R)-tetronate acetate as a biosynthetic intermediate. The X-ray crystal structure of AbyA5, the first of an acetate-eliminating enzyme, reveals a deviant acetyl esterase fold. Molecular dynamics simulations and enzyme assays show the use of a His-Ser dyad to catalyze either elimination or hydrolysis, via disparate mechanisms, under substrate control.

Direct conversion of C6 sugars to methyl glycerate and glycolate in methanol

The present work deals with the one-pot conversion of C6 sugars to methyl glycerate and glycolate via a cascade of retro-aldol condensation and oxidation processes catalyzed by using MoO3 as the Lewis acid catalyst and Au/TiO2 as the oxidation catalyst in methanol. Methyl glycerate (MGLY) is the product of C6 ketose (fructose), while methyl glycolate (MG) is produced from C6 aldose (mannose, glucose). It is found that a good one-pot match between two reactive processes is the key to the production of MGLY and MG with high yield (27.6% MGLY and 39.2% MG). A separated retro-aldol condensation and oxidation process greatly decreases their yields, and even no MGLY can be obtained in this separated process. We attribute this to high instability of glyceraldehyde/glycolaldehyde and their different reaction pathways which mainly depend on whether acetalization of retro-aldol products (glyceraldehyde and glycolaldehyde) occurs with methanol or not. This result opens a new prospect on the accumulation of C3 products other than lactate from biomass-derived carbohydrates.

A Native Ternary Complex Trapped in a Crystal Reveals the Catalytic Mechanism of a Retaining Glycosyltransferase

Glycosyltransferases (GTs) comprise a prominent family of enzymes that play critical roles in a variety of cellular processes, including cell signaling, cell development, and host-pathogen interactions. Glycosyl transfer can proceed with either inversion

A broadly applicable and practical oligomeric (salen)Co catalyst for enantioselective epoxide ring-opening reactions

The (salen)Co catalyst (4a) can be prepared as a mixture of cyclic oligomers in a short, chromatography-free synthesis from inexpensive, commercially available precursors. This catalyst displays remarkable enhancements in reactivity and enantioselectivity relative to monomeric and other multimeric (salen)Co catalysts in a wide variety of enantioselective epoxide ring-opening reactions. The application of catalyst 4a is illustrated in the kinetic resolution of terminal epoxides by nucleophilic ring-opening with water, phenols, and primary alcohols; the desymmetrization of meso epoxides by addition of water and carbamates; and the desymmetrization of oxetanes by intramolecular ring opening with alcohols and phenols. The favorable solubility properties of complex 4a under the catalytic conditions facilitated mechanistic studies, allowing elucidation of the basis for the beneficial effect of oligomerization. Finally, a catalyst selection guide is provided to delineate the specific advantages of oligomeric catalyst 4a relative to (salen)Co monomer 1 for each reaction class.

Characterization of QmnD3/QmnD4 for double bond formation in quartromicin biosynthesis

In this work, two enzymes responsible for the biogenesis of possible [4 + 2] reaction precursors in the quartromicin biosynthetic pathway were characterized: acetylation of 1 to yield 2 was catalyzed by QmnD3, and subsequent acetic acid elimination of 2 to form double bond product 3 was catalyzed by QmnD4. Site-directed mutagenesis assay of QmnD3 and QmnD4 was investigated, and a general base-catalyzed mechanism for QmnD4 is proposed.

Efficient synthesis of dissymmetric malonic acid S, O -esters via monoalcoholysis of symmetric dithiomalonates under neutral conditions

A novel method for the highly selective synthesis of dissymmetric S,O-malonates starting from symmetric diphenyl dithiomalonates under neutral conditions is described. The key step is the thermal formation of an acylketene, the stability of which would co

Orthogonally protected glycerols and 2-aminodiols: Useful building blocks in heterocyclic chemistry

The efficient synthesis of orthogonally protected glycerols, 2-aminopropane-1,3-diols and 2-aminobutane-1,4-diols that can constitute useful tools in heterocyclic chemistry, is reported. These interesting tri-functionalized small synthons were easily prepared from serine or aspartic acid. In addition, these substrates can be readily transformed into their iodide derivatives in very good yields. ARKAT USA, Inc.

Synthetic studies towards 4,10-diaza-1,7-dioxaspiro[5.5]undecanes: access to 3-aza-6,8-dioxabicyclo[3.2.1]octan-2-one and 2H-1,4-oxazin-3(4H)-one frameworks

Synthetic approaches towards 4,10-diaza-1,7-dioxaspiro[5.5]undecanes starting from 1,3-dichloroacetone and solketal derivatives are explored. The method relies on the preparation of a key bis-substituted dihydroxy-protected oxime, which would undergo a final acidic deprotection-spiroacetalization process. Although the desired diazaspiroketal framework could not be obtained, our conditions led to the unexpected 3-aza-6,8-dioxabicyclo[3.2.1]octan-2-one 18 or to the oxazinone 32 in good yields.

d- and l-Serine, useful synthons for the synthesis of 24-hydroxyvitamin D3 metabolites. A formal synthesis of 1α,24R,25-(OH)3-D3, 24R,25-(OH)2-D3 and 24S,25-(OH)2-D3

d- and l-Serine have been used for the enantioselective synthesis of tosylates 7a and 7b, useful building blocks for the synthesis of triols 5a and 5b which have already been obtained via a diastereoselective synthesis and used for the synthesis of 2a, 2b and 2c. We have thus performed a formal synthesis of 24S,25-(OH)2-D3, 24R,25-(OH)2-D3 and 1α,24R,25-(OH)3-D3.