84519-53-9

Basic information

• Product Name: 1,3-Dioxolane-4-carboxaldehyde, 2,2,5-trimethyl-, (4R,5S)- (9CI)
• Synonyms: 1,3-Dioxolane-4-carboxaldehyde, 2,2,5-trimethyl-, (4R,5S)- (9CI)
• CAS NO: 84519-53-9
• Molecular Formula: C₇H₁₂O₃
• Molecular Weight: 144.16838
• Product Categories: ALDEHYDE
• Mol File: 84519-53-9.mol
• Article Data: 21

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1,3-Dioxolane-4-carboxaldehyde, 2,2,5-trimethyl-, (4R,5S)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Dioxolane-4-carboxaldehyde, 2,2,5-trimethyl-, (4R,5S)- (9CI)(84519-53-9)
• EPA Substance Registry System: 1,3-Dioxolane-4-carboxaldehyde, 2,2,5-trimethyl-, (4R,5S)- (9CI)(84519-53-9)

Safety Data

• Hazardous Substances Data: 84519-53-9(Hazardous Substances Data)

Usage

Physical state

Stable, colorless liquid

Usage

Building block in the synthesis of pharmaceuticals and agrochemicals

Stereochemistry

Specific arrangement of atoms in a four-carbon ring structure (4R,5S)

Odor

Pleasant, fruity

Applications

Production of fragrances and flavors, manufacturing of polymers and plastics

Safety

Generally considered safe when handled and used properly, but potential irritant properties require appropriate safety precautions.

Upstream product

• 41167-51-5 (4S,5S)-4-hydroxymethyl-2,2,5-trimethyl-[1,3]-dioxolane 
• 117406-91-4 (2R,3S)-2,3-Dihydroxy-butyric acid methyl ester 
• 102732-59-2 (4R,5S)-(-)-4-(bis-p-tolylthiomethyl)-2,2,5-trimethyl-1,3-dioxolane 
• 159247-46-8 5-Deoxy-3,4-O-isopropyliden-L-lyxitol 
• 73679-53-5 (E,4'S,5'S)-ethyl 3-(2',2',5'-trimethyl-1',3'-dioxolan-4'-yl)acrylate 
• 198009-56-2 ethyl (2E,4S,5S)-4,5-dihydroxy-2-hexenoate 
• 158569-45-0 (4S,5S,2E)-4,5-isopropylidenedioxyhex-2-ene-1-ol 
• 4258-02-0 2,3:5,6-di-O-isopropylidene-D-glucose diethyl dithioacetal 
• 114857-36-2 2,3-O-isopropylidene-D-glucose diethyl dithioacetal 
• 53872-72-3 2,3-O-isopropylidene-L-arabinose diethyl mercaptal 
• 96613-68-2 (2S*,3R*)-methyl 2,3-dihydroxybutanoate 
• 78086-72-3 (2R,3S)-4-desoxy-2,3-O-isopropylidene-L-threonate de methyle 
• 82010-51-3 (4S)-cis-2,2,5-trimethyl-1,3-dioxolane-4-carboxaldehyde 
• 36183-27-4 cis-2,2,5-Trimethyl-1,3-dioxolan-4-carbonsaeure-methylester 

Downstream Products

• 41167-51-5 (4S,5S)-4-hydroxymethyl-2,2,5-trimethyl-[1,3]-dioxolane 
• 96613-69-3 (4-Methoxy-phenyl)-[1-((4S,5S)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-meth-(Z)-ylidene]-amine 
• 73656-92-5 methyl (3S,4S,5S)-3-benzoylamino-4,5-(isopropylidenedioxy)hexanoate 
• 111554-02-0 tert-butyl (3S,4S,5S)-3--4,5-(isopropylidenedioxy)hexanoate 
• 111524-24-4 methyl (3S,4S,5S)-3--4,5-(isopropylidenedioxy)hexanoate 
• 111524-17-5 methyl (4S,5S)--4,5-(isopropylidenedioxy)hexanoate 
• 111524-19-7 tert-butyl (4S,5S)-3--4,5-(isopropylidenedioxy)hexanoate 
• 111524-22-2 tert-butyl (4S,5S)-3--4,5-(isopropylidenedioxy)hexanoate 
• 111524-25-5 methyl (4S,5S)-3--4,5-(isopropylidenedioxy)hexanoate 
• 111524-21-1 methyl (4S,5S)-3--4,5-(isopropylidenedioxy)hexanoate 
• 1393793-01-5 tert-butyl (S,S,S)-3-(N-benzyl-N-isopropylamino)-4,5-O-isopropylidene-4,5-dihydroxyhexanoate 
• 1393793-02-6 tert-butyl (3R,4S,5S)-3-(N-benzyl-N-isopropylamino)-4,5-O-isopropylidene-4,5-dihydroxyhexanoate 
• 1393793-05-9 tert-butyl (3S,4S,5S,αR)-3-[N-benzyl-N-(α-methylbenzyl)amino]-4,5-O-isopropylidene-4,5-dihydroxyhexanoate 
• 1393793-06-0 tert-butyl (3R,4S,5S,αR)-3-[N-benzyl-N-(α-methylbenzyl)amino]-4,5-O-isopropylidene-4,5-dihydroxyhexanoate 

Relevant articles and documents

Versicolactones A and B: Total synthesis and structure revision

To further determine absolute configurations of versicolactones A and B, total synthesis of versicolactones A and B and their six stereoisomers were reported in this Letter. The 1H and 13C NMR spectra of the synthetic erythro-stereoisomers matched perfectly with those of the natural products. Combined with the comparison of the specific rotations, the absolute configuration of versicolactones A and B were revised as (4Z,6R,7S)- and (4E,6R,7S)- from the corresponding (4Z,6R,7R)- and (4E,6R,7R)-6,7-dihydroxyocta- 2,4-dien-4-lactone, respectively.

Synthesis and bioluminescence-inducing properties of autoinducer (S)-4,5-dihydroxypentane-2,3-dione and its enantiomer

The autoinducer (4S)-4,5-dihydroxypentane-2,3-dione ((S)-DPD, AI-2) facilitates chemical communication, termed 'quorum sensing', amongst a wide range of bacteria, The synthesis of (S)-DPD is challenging in part due to its instability. Herein we report a novel synthesis of (S)-DPD via (2S)-2,3-O-isopropylidene glyceraldehyde, through Wittig, dihydroxylation and oxidation reactions, with a complimentary asymmetric synthesis to a key precursor. Its enantiomer (R)-DPD, was prepared from d-mannitol via (2R)-2,3-O-isopropylideneglyceraldehyde. The synthesized enantiomers of DPD have AI-2 bioluminescence-inducing properties in the Vibrio harveyi BB170 strain.

Synthesis of β,γ-disubstituted-γ-lactones through a Johnson-Claisen rearrangement: a short route to xylobovide, nor-canadensolide, canadensolide, sporothriolide and santolinolide

The Johnson-Claisen rearrangement of allyl alcohols with chiral vicinal diol functionality was employed to access chiral β,γ-disubstituted-γ-lactones in high enantio- and diastereoselectivity. These were efficiently converted into nor-canadensolide, the advanced γ-(lactone-lactol) intermediate for xylobovide, canadensolide and sporothriolide and the lactone moiety of the santolinolides.