41167-51-5

Usage

Uses

Used in Organic Synthesis:
[(4R,5S)-2,2,5-trimethyl-1,3-dioxolan-4-yl]methanol is used as a building block for the synthesis of complex organic molecules, leveraging its unique reactivity and structural features to facilitate the creation of novel compounds.
Used in Pharmaceutical Research:
In the pharmaceutical industry, [(4R,5S)-2,2,5-trimethyl-1,3-dioxolan-4-yl]methanol serves as a key intermediate in the development of new drugs, thanks to its potential to be modified and incorporated into a wide range of medicinal compounds.
Used as a Solvent:
[(4R,5S)-2,2,5-trimethyl-1,3-dioxolan-4-yl]methanol is utilized as a solvent in various chemical reactions, providing a suitable medium for the reactants to mix and interact, thus facilitating the desired chemical transformations.
Used as a Reagent:
[(4R,5S)-2,2,5-trimethyl-1,3-dioxolan-4-yl]methanol also functions as a reagent, participating directly in chemical reactions to produce the desired products, taking advantage of its specific chemical properties.
It is crucial to handle [(4R,5S)-2,2,5-trimethyl-1,3-dioxolan-4-yl]methanol with care due to its potential health hazards if not properly managed.

Upstream product

• 81704-65-6 ethyl erythro-2,3-O-isopropylidenedioxybutyrate 
• 81704-65-6 ethyl threo-2,3-O-isopropylidenedioxybutyrate 
• 58829-89-3 (4R,5S)-2,2-dimethyl-4-iodomethyl-5-hydroxymethyl-1,3-dioxolane 
• 78086-72-3 (2R,3S)-4-desoxy-2,3-O-isopropylidene-L-threonate de methyle 
• 59779-75-8 diethyl (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate 
• 1393792-92-1 (S,S)-2,2-dimethyl-4-(tert-butyldimethylsilyloxy)methyl-5-methyl-1,3-dioxolane 
• 108817-96-5 [(4S,5S)-5-[(tert-butyl(dimethyl)silyl)oxymethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]methanol 
• 114826-50-5 (4R,5S)-2,2-dimethyl-4-iodomethyl-5-benzyloxymethyl-1,3-dioxolane 
• 85446-27-1 erythro-3-amino-1,2-butanediol 
• 67-64-1 acetone 
• 84519-53-9 (4R,5S)-2,2,5-trimethyl-1,3-dioxolane-4-carbaldehyde 
• 87-91-2 diethyl (2R,3R)-tartrate 
• 77-76-9 2,2-dimethoxy-propane 
• 78469-77-9 (4S,5S)-4-benzyloxymethyl-5-hydroxymethyl-2,2-dimethyl-1,3-dioxolane 

Downstream Products

• 73987-14-1 Toluene-4-sulfonic acid 2,2,5-trimethyl-[1,3]dioxolan-4-ylmethyl ester 
• 73987-14-1 Toluene-4-sulfonic acid 2,2,5-trimethyl-[1,3]dioxolan-4-ylmethyl ester 
• 73987-14-1 (-)-1-O-p-toluenesulfonyl-4-deoxy-2,3-O-isopropylidene-L-threytol 
• 84519-53-9 (4R,5S)-2,2,5-trimethyl-1,3-dioxolane-4-carbaldehyde 
• 111524-20-0 C₂₆H₄₅NO₅Si 
• 111524-18-6 C₂₃H₃₉NO₅Si 
• 111524-17-5 C₂₃H₃₉NO₅Si 
• 111687-35-5 C₂₄H₄₁NO₅Si 
• 125257-84-3 C₂₄H₄₁NO₅Si 
• 111524-21-1 C₂₄H₄₁NO₅Si 
• 111524-23-3 C₂₇H₄₇NO₅Si 
• 111524-22-2 C₂₇H₄₇NO₅Si 
• 111524-26-6 C₂₉H₄₃NO₅Si 
• 111524-25-5 C₂₉H₄₃NO₅Si 

Relevant academic research and scientific papers

Enantioselective sensing of insect pheromones in water

An arrayed combination of water-soluble deep cavitands and cationic dyes has been shown to optically sense insect pheromones at micromolar concentration in water. Machine learning approaches were used to optimize the most effective array components, which

The revised structure of trichodermatide A

A revised structure for trichodermatide A, which is a C10 epimer of the originally reported structure, is proposed. The revision is supported by the X-ray structure of a synthetic intermediate synthesized according to our previous route for trichodermatide A. The revised stereochemistry was also supported by NOESY experiment. Finally, we synthesized Trauner's compound corresponding to the originally reported structure from our synthetic intermediate of trichodermatide A through a Mitsunobu reaction at C10. A revised structure for trichodermatide A is proposed. The revision is supported by the X-ray structure of a synthetic intermediate synthesized according to our previous route for trichodermatide A. The revised stereochemistry was also supported by NOESY experiment. Finally, we synthesized Trauner's compound corresponding to the originally reported structure from our synthetic intermediate of trichodermatide A through a Mitsunobu reaction at C10.

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.

On the origins of diastereoselectivity in the conjugate additions of the antipodes of lithium N-benzyl-(N-α-methylbenzyl)amide to enantiopure cis- and trans-dioxolane containing α,β-unsaturated esters

"Matching" and "mismatching" effects in the doubly diastereoselective conjugate additions of the antipodes of lithium N-benzyl-(N-α-methylbenzyl)amide to enantiopure cis- and trans-dioxolane containing α,β-unsaturated esters have been investigated. High levels of substrate control were established first upon conjugate addition of achiral lithium N-benzyl-N-isopropylamide to both tert-butyl (S,S,E)-4,5-O- isopropylidene-4,5-dihydroxyhex-2-enoate and tert-butyl (4R,5S,E)-4,5-O- isopropylidene-4,5-dihydroxyhex-2-enoate. However, upon conjugate addition of lithium (R)-N-benzyl-(N-α-methylbenzyl)amide and lithium (S)-N-benzyl-(N-α-methylbenzyl)amide to these substrates, neither reaction pairing reinforced the apparent sense of substrate control. These reactions do not, therefore, conform to the classical doubly diastereoselective "matching" or "mismatching" pattern usually exhibited by this class of reaction. A comparison of these reactions with the previously reported doubly diastereoselective conjugate addition reactions of lithium amide reagents to analogous substrates is also discussed.

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.

Total synthesis of (+)-varitriol

The total synthesis of natural (+)-varitriol (1) was accomplished by starting from dimethyl L-tartrate. The key features were a substrate selective and diastereoselective PdII-catalysed bicyclisation of unsaturated protected triol 9 followed by regioselective ring-opening of bicyclic skeleton 10. The absolute configuration of the target was confirmed by single-crystal X-ray analysis for the first time.

Stereoselective synthesis of 1,2-13C2-L-fucose, 1,2-13C2-fucono-γ-lactone and 1,2- 13C2-fucono-γ-lactol from non-sugar starting material

An efficient synthesis is reported for the preparation of L-fucose, and of L-fucofuranose, from 1. The route is designed to facilitate 13C labelling at C1 and/or C2, and the synthesis of 1,2-13C 2-fucose as its tetraacetate is described. The C2 and C3 stereo-centres are introduced using asymmetric dihydroxylation, and the lactone ring size resulting from cyclisation of 4 was controlled to provide the L-fucofuranone 5, whose structure was unambiguously established by X-ray crystal analysis of the derived trisilyl ether 6. Generation of the fucose lactol 7 by reduction of 6 followed by deprotection then provided L-fucose, isolated as its peracetate 8. Georg Thieme Verlag Stuttgart.

The use of π-allyltricarbonyliron lactone complexes in the synthesis of the resorcylic macrolides α- and β-zearalenol

A highly stereoselective synthesis of the natural products α- and β-zearalenol 1 and 2 has been achieved using π-allyltricarbonyliron lactone complexes to control the 1,5-stereochemical relationship of the oxygen functionalities found in these resorcylic macrolides.

On the selectivity of oxynitrilases towards α-oxygenated aldehydes

Different α-alkoxy and α,β-di-alkoxy substituted aldehydes have been submitted to the catalytic action of the oxynitrilases from almond (PaHNL) or from Hevea brasiliensis (HbHNL), in order to explore the possibility of using these enzymes for the preparation of complex cyanohydrins. The selectivity of both enzymes towards these compounds was found to be largely dependent on the substitutents, being low with the aldehydes carrying the sterically more demanding phenyl substituent. Contrary to the chemical addition of HCN, which always occurs with a slight preference for the formation of the anti diastereoisomers, the enzymatic cyanuration - occurring with a facial preference, Si or Re according to the biocatalyst used - gave a mixture of cyanohydrins that, depending on the starting enantiomeric aldehyde, can be enriched in the syn diastereoisomers.

The use of π-allyltricarbonyliron lactone complexes in the synthesis of the resorcylic macrolides α- and β-zearalenol

A highly stereoselective synthesis of α- and β-zearalenol 1 and 2 is accomplished utilising π-allyltricarbonyliron lactone complexes 5 and 6 to establish the 1,5-stereochemical relationship of oxygen functionalities present in the natural products. The Royal Society of Chemistry 2000.