5736-03-8

Usage

Uses

Used in Synthetic Organic Chemistry:
2,2-Dimethyl-1,3-dioxolane-4-carboxaldehyde is used as a chemical intermediate for the synthesis of other compounds. Its unique structure and functional groups make it a valuable component in the creation of various organic molecules.
Due to the limited information provided on its safety profiles, environmental, and health impacts, it is essential to handle 2,2-Dimethyl-1,3-dioxolane-4-carboxaldehyde with caution and conduct further research to understand its properties and effects better.

InChI:InChI=1/C6H10O3/c1-6(2)8-4-5(3-7)9-6/h3,5H,4H2,1-2H3

Upstream product

• 56-82-6 Glyceraldehyde 
• 67-64-1 acetone 
• 100-79-8 (R,S)-2,2-dimethyl-1,3-dioxolane-4-methanol 
• 53735-98-1 1,2:5,6-di-O-isopropylidene-D-glucitol 
• 312583-58-7 (1S,2S)-1,2-bis(2,2-dimethyl-1,3-dioxolan-4-yl)ethane-1,2-diol 
• 82188-74-7 O¹,O²;O⁵,O⁶-diisopropylidene-mannitol 
• 53735-98-1 (1S,2S)-1,2-bis[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]ethane-1,2-diol 
• 116-11-0 2-Methoxypropene 
• 61821-85-0 (2,2-Dimethyl-[1,3]dioxolan-4-yl)-ethanol 
• 77-76-9 2,2-dimethoxy-propane 
• 1707-77-3 1,2:5,6-di-O-isopropylidene-D-mannitol 
• 860649-42-9 5,6-0-isopropylidene ascorbic acid 
• 22323-78-0 (1R,2R)-1,2-bis((S)-2,2-dimethyl-1,3-dioxolan-4-yl)ethane-1,2-diol 
• 126694-15-3 4,5-isopropylidene-D-arabinose dibenzyl thioacetal 

Downstream Products

• 110598-85-1 [(R)-1-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-allyloxy]-methyl-diphenyl-silane 
• 110598-85-1 [(R)-1-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-allyloxy]-methyl-diphenyl-silane 
• 141887-87-8 2,2-Dimethyl-4-((E)-4-phenyl-but-1-enyl)-[1,3]dioxolane 
• 142696-31-9 (E)-2-Benzyloxycarbonylamino-3-(2,2-dimethyl-[1,3]dioxolan-4-yl)-acrylic acid methyl ester 
• 142696-32-0 (Z)-2-Benzyloxycarbonylamino-3-(2,2-dimethyl-[1,3]dioxolan-4-yl)-acrylic acid methyl ester 
• 86559-77-5 Benzoic acid cyano-(2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl ester 
• 103773-42-8 4,5-O-isopropylidene-2-pentenal 
• 105662-92-8 (Z)-N-(2,2-dimethyl-1,3-dioxolan-4-yl)methylenebenzylamine N-oxide 
• 84629-17-4 1-(2,2-Dimethyl-1,3-dioxolan-4-yl)-4-phenyl-1,4-butandion 
• 90493-96-2 2,2-dimethyl-1,3-dioxolane-4-carboxylic acid chloride 
• 100289-50-7 (E)-(4'S)-2-(2',2'-dimethyl-1',3'-dioxalan-4'-yl)vinyl phenyl sulphone 
• 100289-51-8 (Z)-(4'S)-2-(2',2'-dimethyl-1',3'-dioxalan-4'-yl)vinyl phenyl sulphone 
• 128525-69-9 (±)-ethyl trans-3-(2,2-dimethyl-1,3-dioxolan-4-yl)propenoate 
• 17510-99-5 4,5,6-trihydroxy-2-oxohexanoic acid 

Relevant academic research and scientific papers

Preparation method of antitumor drug gemcitabine hydrochloride

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Chemoenzymatic Access to Chiral Tetrols Produced by Thiamine Diphosphate Dependent Benzaldehyde Lyase

Highly functionalized polyol building blocks have been synthesized by means of stereoselective chemoenzymatic C–C bond formation followed by stereoselective reduction. Catalysis by thiamine diphosphate (ThDP) dependent benzaldehyde lyase (BAL) with glyceraldehyde acetonide as acceptor substrate gave highly stereoenriched polyols such as (1S,2S,3R)-1-phenylbutane-1,2,3,4-tetrol (1), the 3,4-protected anti-1,2-diol 5, and the precursor of both compounds, 2-hydroxyketone 4.

Method for catalytic synthesis for glyceraldehyde acetonide

The invention relates to a method for catalytic synthesis for glyceraldehyde acetonide. The method specifically comprises the following steps: dissolving glycerol acetonide into acetone, adding a proper amount of a fullerene zinc oxide selenium (C60/ZnO/Se) composite material, introducing oxygen to carry out a reaction at a room temperature till a reaction liquid has no glycerol acetonide, centrifuging to remove the fullerene zinc oxide selenium (C60/ZnO/Se) composite material, carrying out vacuum concentration on supernate, and drying to obtain the glyceraldehyde acetonide.

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Synthesis of Cryptochiral (R,R)-2,3-Dideuterooxirane as Stereochemical Reference Compound and Chemical Correlation with D-(+)-Glyceraldehyde

Chirality plays a pivotal role in chemistry and biology, e.g., structure-specific targeting in drug development or the lock-and-key theory of enzyme interactions. Determining absolute configurations of chiral molecules is essential to understanding such mechanisms and to developing chemical processes involving chiral compounds. In particular, this becomes obvious in the understanding of chemical reaction networks in the context of the origins of life. A stereochemical reference compound that can be correlated with sugars, amino acids, etc. is of great interest. Here, we present the synthesis of enantiopure (R,R)-2,3-dideuterooxirane, of which the absolute configuration has been unambiguously determined by foil-induced Coulomb explosion imaging, and the correlation with the configuration of D-(+)-glyceraldehyde.

Oxoammonium salt oxidations of alcohols in the presence of pyridine bases

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Coulomb explosion imaged cryptochiral (R,R)-2,3-dideuterooxirane: Unambiguous access to the absolute configuration of (+)-glyceraldehyde

The absolute configuration of (R,R)-2,3-dideuterooxirane, which has been independently determined using Coulomb explosion imaging, has been unambiguously chemically correlated with the stereochemical key reference (+)-glyceraldehyde. This puts the absolute configuration of D(+)-glyceraldehyde on firm experimental grounds. 100% Absolute: The absolute configuration of (R,R)-2,3-dideuterooxirane, which has been independently determined by Coulomb explosion imaging (CEI), has been unambiguously chemically correlated with the stereochemical key reference (+)-glyceraldehyde. This puts the absolute configuration of D(+)-glyceraldehyde on firm experimental grounds (see scheme).

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SUBSTITUTED BENZOAZEPINES AS TOLL-LIKE RECEPTOR MODULATORS

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Stereoselective triplet-sensitised radical reactions of furanone derivatives

The stereo- and regioselectivity of triplet-sensitised radical reactions of furanone derivatives have been investigated. Furanones 7a,b were excited to the 3ππ* state by triplet energy transfer from acetone. Intramolecular hydrogen abstraction then occurred such that hydrogen was transferred from the tetrahydropyran to the β position of the furanone moiety. Radical combination of the tetrahydropyranyl and the oxoallyl radicals led to the final products 8a,b. In the intramolecular reaction, overall, a pyranyl group adds to the a position of the furanone. The effect of conformation was first investigated with compounds 9a,b carrying an additional substituent on the tether between the furanone and pyranyl moiety. Further information on the effect of conformation and the relative configuration at the pyranyl anomeric centre and the furanone moiety was obtained from the transformations of the glucose derivatives 12, 14, 17 and 18. Radical abstraction occurred at the anomeric centre and at the S′-position of the glucosyl moiety. Computational studies of the hydrogen-abstraction step were carried out with model structures. The activation barriers of this step for different stereoisomers and the abstraction at the anomeric centre and at the 6' -position of the tetrahydropyranyl moiety were calculated. The results of this investigation are in accordance with experimental observations. Furthermore, they reveal that the reactivity and regioselectivity are mainly determined in the hydrogen-abstraction step. Intramolecular hydrogen abstraction (almost simultaneous electron and proton transfer) in 3ππ * excited furanones only takes place under restricted structural conditions in a limited number of conformations that are defined by the relative configuration of the substrates. It is observed that in the biradical intermediate, back-hydrogen transfer occurs leading to the starting compound. In the case of glucose derivatives, this reaction led to epimerisation at the anomeric centre.