15667-21-7

Usage

Uses

Used in Pharmaceutical Industry:
D-ERYTHRONOLACTONE is used as a chiral synthon for the synthesis of certain natural products, such as the leukotrienes. Its role in the pharmaceutical industry is crucial for the development of new drugs and therapeutic agents that target various health conditions.
Used in Biochemical Research:
As a potential substrate of dihydroxy acid dehydratase, D-ERYTHRONOLACTONE plays a significant role in biochemical research. It aids in understanding the enzyme's function and its involvement in various metabolic pathways, which can lead to the discovery of novel treatments for specific diseases.
Used in Chemical Synthesis:
D-ERYTHRONOLACTONE's unique chemical properties make it an essential compound in chemical synthesis. It serves as a key building block for the creation of various complex molecules and compounds, contributing to the advancement of materials science and the development of new products with diverse applications.

Purification Methods

Recrystallise it from EtOAc (20 parts) or isoPrOH (3 parts). [Baker & MacDonald J Am Chem Soc 82 230 1960, Glattfeld & Forbrich J Am Chem Soc 56 1209 1934, Weidenhagen & Wegner Chem Ber 72 2010 1939, Musich & Rapoport J Am Chem Soc 100 4865 1978, Beilstein 18/2 V 457.]

InChI:InChI=1/C4H6O4/c5-2-1-8-4(7)3(2)6/h2-3,5-6H,1H2/t2-,3-/m1/s1

Upstream product

• 488-16-4 D-erythronic acid 
• 141316-88-3 (2R,3S)-2,3-O-cyclohexylideneerythritol monoacetate 
• 89-65-6 isoascorbic acid 
• 7152-74-1 (-)-(3R-cis)-mono(tetrahydro-4-hydroxy-2-oxo-3-furanyl)ester 2-(4-methyl-phenyl)hidrazide of ethanedioic acid 
• 50-81-7 D-Isoascorbic acid 
• 488-16-4 (+/-)-erythronic acid 
• 219788-23-5 1,2:3,4-Di-O-isopropylidene-D-erythronic acid 
• 164385-70-0 (R)-(tert-Butyl-dimethyl-silanyloxy)-((R)-2,2-diethyl-[1,3]dioxolan-4-yl)-acetic acid methyl ester 
• 134-03-2 Erythorbic acid 
• 10323-20-3 D-Arabinose 
• 25581-41-3 D-erythronolactone acetonide 
• 50-81-7 ascorbic acid 
• 2418-52-2 D-threitol 
• 909878-64-4 meso-erythritol 

Downstream Products

• 89299-65-0 methyl (2R,3R)-2,3,4-trihydroxybutanoate 
• 130412-79-2 (2R,3R)-2,3-bis(benzyloxy)-4-hydroxybutanoic acid 1,4-lactone 
• 136060-76-9 2-O-Tosyl-D-erythro-1,4-lactone 
• 136060-77-0 Toluene-4-sulfonic acid 2-oxo-2,5-dihydro-furan-3-yl ester 
• 25581-41-3 D-erythronolactone acetonide 
• 107-93-7 (E)-but-2-enoic acid 
• 7425-21-0 3-Iodo-n-butanoic acid 
• 488-16-4 D-erythronic acid 
• 169738-13-0 2,3-O-(R)-benzylidene-D-erythronolactone 
• 169561-50-6 2-O-benzyl-D-erythronolactone 
• 189996-59-6 (4R,5R)-5-Hydroxymethyl-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid methyl ester 
• 188251-56-1 (3R,4R)-3-(tert-Butyl-diphenyl-silanyloxy)-4-hydroxy-dihydro-furan-2-one 
• 78646-86-3 2-(5H)-furanon-3-yl methanesulfonate 
• 28875-69-6 2,3-O-cyclohexylidene-α-D-erythronolactone 

Relevant academic research and scientific papers

Enzyme-catalyzed asymmetric synthesis; 10. Pseudomonas cepacia lipase mediated synthesis of enantiomerically pure (2R,3S)- and (2S,3R)-2,3-O-cyclohexylideneerythritol monoacetate from 2,3-O-cyclohexylideneerythritol

Pseudomonas cepacia lipase catalyzed hydrolysis of 2,3-O-cyclohexylideneerythritol diacetate in an emulsion of water and diisopropyl ether gives (2S,3R)-2,3-O-cyclohexylideneerythritol monoacetate [(2S,3R)-1-acetoxy-2,3-cyclohexylidenedioxy-4-hydroxybutane] with ≥ 99% ee in 91% yield by a preferential attack at the R-center CH2OAc group. The enantiomeric (2R,3S)-2,3-O-cyclohexylideneerythritol monoacetate is obtained by acetylation of 2,3-O-cyclohexylideneerythritol with vinyl acetate catalyzed by the same enzyme with ≥ 99% ee in 78% yield by a combined enantiotopos and enantiomer differentiation through a preferential attack at the R-center CH2OH groups.

Asymmetric induction in intramolecular [2 + 2]-photocycloadditions of 1,3-disubstituted allenes with enones and enoates

Irradiation of optically active allenes (89-92% ee) appended to enones and enoates affords alkylidenecyclobutane photoadducts with high levels of asymmetric induction (83-100%) derived exclusively from the allene fragment. The substrates studied include allenes tethered to enones such as 1,3-cyclohexanedione and 1,3-cyclopentanedione, as well as allenes tethered to functionalized coumarins. The enantiomer ratios of the photoadducts were quantified by derivatization of the products as the corresponding Mosher MTPA esters and analysis by 1H NMR spectroscopy. The exo-methylenecyclobutanes obtained upon irradiation of allene-coumarins are isolated as single olefin diastereomers. Irradiation of a coumarin tethered at C(5) with an optically active allene affords an alkynyl-substituted oxepane with complete asymmetric induction.

Toward the stereoselective synthesis of zaragozic acid framework: A desilylation-aldol reaction approach

A convergent synthesis of the C3-C8 fragment of zaragozic acids is described. The key reactions include desilylation-aldol reaction, rearrangement induced by regioselective reductive cleavage, BAIB/TEMPO-Pinnick oxidation, esterification, silylation, and hydrogenolysis.

General Synthetic Approach to Rotenoids via Stereospecific, Group-Selective 1,2-Rearrangement and Dual S N Ar Cyclizations of Aryl Fluorides

A general synthetic approach to rotenoids is described, featuring 1) stereospecific, group-selective 1,2-rearrangements of epoxy alcohols, and 2) S N Ar oxy-cyclizations of aryl fluorides. The common intermediate epoxyketone, en route to (-)-rotenone and (-)-deguelin, was prepared from d -araboascorbic acid in five steps. Also described is the conversion of (-)-deguelin into oxidized congeners, (-)-tephrosin and (+)-12a- epi -tephrosin.

Synthesis of threo- and erythro-configured trihydroxy open chain lipophilic ketones as possible anti-mycobacterial agents

A series of threo- and erythro-configured open-chain trihydroxy ketones was synthesized starting from L- and D-ascorbic acid respectively as the starting material, through the use of Grignard reactions for the requisite C[sbnd]C bond formations. The lipophilic ketones were screened against Mycobacteriumtuberculosis for anti-proliferative activity. The lipophilic ketones with tetradecyl alkyl side chains were found to be moderately active against cell proliferation.

A method for synthesizing tetranoic acid

The invention discloses a synthetic method of tetronic acid. The synthetic method comprises the following steps: firstly oxidizing low-price easily-available natural sodium D-isoascorbate as a raw material through hydrogen peroxide, and acidifying through hydrochloric acid to prepare a key synthetic intermediate, namely erythronolactone; secondly, reacting erythronolactone with sulfonyl chloride to generate crude tetronic acid; finally, simply re-crystallizing obtained crude tetronic acid to obtain pure tetronic acid. The synthetic method has the characteristics of few synthetic steps, simple and convenient process, low synthetic cost, convenience for large-scale industrialized production and the like; finally obtained pure tetronic acid is high in yield and purity, the yield can reach more than 87%, and the purity can reach more than 99%.

Benzoxazol and oxazine ketone compounds and intermediates for the preparation of crystalline form and (by machine translation)

A preparation method for a high-purity benzoxazoleoxazine ketone compound, a crystal form thereof, and an intermediate compound for preparing a compound of formula (I), and a preparation method therefor.

Unexpected facile synthesis of tetronic acid during the research on stereospecific total synthesis of (+)-biotin starting from D-erythorbic acid as chiral pool

The reaction of D-erythronolactone (8) with the methanesulfonyl chloride in the presence of triethylamine afforded, after unexpected elimination reaction, the tetronic acid is obtained in excellent yield and chemical purity, instead of the dimesylates (7)

Doubly diastereoselective conjugate additions of the antipodes of lithium N-benzyl-N-(α-methylbenzyl)amide to enantiopure ε-O-protected α,β-unsaturated esters derived from d-ribose

Enantiopure ε-O-silyloxy- and ε-O-benzyloxy-α,β- unsaturated esters derived from d-ribose, each containing a cis-dioxolane unit, display excellent (≥95:5 dr) levels of diastereofacial directing ability upon conjugate addition of achiral lithium N-benzyl-N-isopropylamide. In contrast to the corresponding enantiopure ε-O-silyloxy-α,β-unsaturated ester derived from l-tartaric acid, which contains a trans-dioxolane unit, the conjugate additions of the antipodes of lithium N-benzyl-N-(α- methylbenzyl)amide to its cis-configured counterpart result in doubly diastereoselective 'matched' and 'mismatched' reaction pairings in which the inherent reagent control serves to augment or oppose, respectively, the established substrate diastereocontrol.

Synthetic studies towards an advanced precursor of the jatrophane diterpene Pl-4

Jatrophane diterpenes, isolated from members of the Euphorbiaceae plant family, constitute a class of biologically and structurally intriguing natural products. Herein, different strategies for the preparation of an advanced intermediate towards the total synthesis of the jatrophane diterpene Pl-4 are described. Key strategies for the elaboration of the jatrophane precursors include hydrometalation and radical reactions. Georg Thieme Verlag KG Stuttgart · New York.