15909-76-9

Basic information

• Product Name: methyl 2,3-dihydroxypropanoate
• Synonyms: propanoic acid, 2,3-dihydroxy-, methyl ester; Propanoic acid, 2,3-dihydroxy-, methyl ester, (+-)-
• CAS NO: 15909-76-9
• Molecular Formula: C₄H₈O₄
• Molecular Weight: 120.1039
• Mol File: 15909-76-9.mol
• Article Data: 69

Chemical Properties

• Boiling Point: 241.5°C at 760 mmHg
• Flash Point: 103.7°C
• Density: 1.285g/cm³
• Vapor Pressure: 0.00616mmHg at 25°C
• Refractive Index: 1.455
• CAS DataBase Reference: methyl 2,3-dihydroxypropanoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 2,3-dihydroxypropanoate(15909-76-9)
• EPA Substance Registry System: methyl 2,3-dihydroxypropanoate(15909-76-9)

Safety Data

• Hazardous Substances Data: 15909-76-9(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 57-48-7 D-Fructose 
• 4538-50-5 methyl glycidate 
• 198572-71-3 N-(tert-butoxycarbonyl)-2-nitrobenzenesulfonamide 
• 473-81-4 (S)-glyceric acid 
• 473-81-4 D-glyceric acid 
• 149-73-5 trimethyl orthoformate 
• 292638-85-8 acrylic acid methyl ester 
• 312-84-5 D-Serine 
• 52373-72-5 methyl (R)-2,2-dimethyl-1,3-dioxolane-4-carboxylate 
• 473-81-4 glyceric acid 
• 56-81-5 glycerol 
• 186581-53-3 diazomethane 
• 108865-84-5 methyl 2,2-dimethyl-1,3-dioxolane-4-carboxylate 

Downstream Products

• 52373-72-5 methyl (R)-2,2-dimethyl-1,3-dioxolane-4-carboxylate 
• 14028-62-7 D-glyceric acid, calcium salt 
• 60456-21-5 methyl (4S)-2,2-dimethyl-1,3-dioxolane-4-carboxylate 
• 108865-84-5 methyl 2,2-dimethyl-1,3-dioxolane-4-carboxylate 
• 77522-15-7 (2R)-2,3-dihydroxy-3-methylbutan-1-yl p-toluenesulfonate 
• 93306-88-8 methyl 2-benzyloxy-3-hydroxypropionate 
• 98291-97-5 methyl 2-hydroxy-3-(benzyloxy)propionate 
• 137618-50-9 2,3-dihydroxy-N,N-dimethylpropionamide 
• 20869-41-4 methyl (2S)-2,3-di-O-benzoylglycerate 
• 14028-63-8 L-glyceric acid hemicalcium salt 
• 55032-33-2 (R)-2-phenyl-[1,3,2]dioxaborolane-4-carboxylic acid methyl ester 
• 55032-29-6 (R)-2-(4-vinyl-phenyl)-[1,3,2]dioxaborolane-4-carboxylic acid methyl ester 
• 16814-88-3 methyl (2R)-2-methoxy-3-(triphenylmethoxy)propanoate 

Relevant articles and documents

Synthesis of Alkyl (+/-)-2,3-Di-O-acylglycerates and Attempts Directed to their Conversion into Alkyl (R)-2,3-Di-O-acylglycerates by Enzyme-catalyzed Enantioselective Deacylation Reactions

By screening several lipases and proteases as catalysts for an enantioselective partial deacylation of methyl (+/-)-2,3-di-O-acylglycerates, it was found that methyl (R)-2,3-di-butanoylglycerate can be obtained with an enantiomeric excess of >96percent and a yield of 20percent related to the racemic starting material.This was prepared from methyl acrylate through dihydroxylation with potassium permanganate at -30 deg C and a subsequent bisacylation.

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.

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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.

Concise Asymmetric Synthesis of Kweichowenol A

An asymmetric 11-step synthesis of the polyoxygenated cyclohexene natural product kweichowenol A from the traditional Chinese medicinal herb Uvaria kweichowesis is reported. The oxygenation pattern was installed on a linear precursor by exploiting the acyclic stereocontrol of the Kiyooka aldol reaction, as well as Cram chelate-controlled Grignard reactions. Ring-closing metathesis and a selective benzoylation then gave the natural product.