190912-15-3

Usage

Also known as

2-methyl-2,3-dihydropyran-4-one

Physical properties

colorless liquid with a fruity odor

Common uses

flavor and fragrance ingredient in the food and beverage industry

Applications

building block in the synthesis of pharmaceuticals, agrochemicals, and other organic compounds

Additional properties

antioxidant properties, potential applications in medicine and skincare

Upstream product

• 80754-64-9 (6-Methoxy-2-methyl-3,6-dihydro-2H-pyran-4-yloxy)-trimethyl-silane 
• 82456-95-9 (1R,2S,6R)-2-Methoxy-4-methyl-3,7-dioxa-bicyclo[4.1.0]heptane 
• 54125-02-9 danishefsky's diene 
• 75-07-0 acetaldehyde 
• 194233-66-4 (1E)-3-{[tert-butyl(dimethyl)silyl]oxy}-N,N-dimethyl-1,3-butadien-1-amine 
• 1085182-72-4 2-triethylsiloxy-4-methoxy-1,3-butadiene 
• 869293-25-4 (R)-5-((tert-butyldimethylsilyl)oxy)hex-1-en-3-one 
• 1393537-60-4 (E)-5-((R)-tert-butyldimethylsilyloxy)-1-(piperidin-1-ylimino)hexan-3-one 
• 1202377-99-8 (S)-4-methoxyhexa-4,5-dien-2-ol 
• 548440-36-4 (S)-5-((tert-butyldimethylsilyl)oxy)hex-1-en-3-one 
• 1202377-94-3 C₈H₁₄O₄ 
• 2232-58-8 (Z)-6-Methoxy-hex-5-en-3-yn-2-ol 

Downstream Products

• 14505-80-7 (+/-)-trans-2,6-dimethyltetrahydropyran-4-one 
• 14505-80-7 (2S,6S)-2,6-dimethyl-3,4,5,6-tetrahydro-2H-pyran-4-one 
• 1202377-97-6 (S)-2-methyltetrahydropyran-4-ol 
• 82110-21-2 (S)-2-methyl-3,4,5,6-tetrahydro-2H-pyran-4-one 
• 1053231-38-1 (2R,6R)-2,6-dimethyldihydro-2H-pyran-4(3H)-one 
• 752244-29-4 (2R,6S)-2,6-dimethyltetrahydro-4H-pyran-4-one 
• 82110-22-3 (2R)-2-methyltetrahydro-4H-pyran-4-one 

Relevant academic research and scientific papers

Scalable De Novo Synthesis of Aldgarose and Total Synthesis of Aldgamycin N

Since the accompanying study had shown that the introduction of the eponymous aldgarose sugar to the C5-OH group of the macrocyclic aglycone of aldgamycin N is most difficult, if not even impossible, the synthesis route was revised and the glycosidation performed at an earlier stage. To mitigate the “cost” of this strategic amendment, a practical and scalable de novo synthesis of this branched octose was developed. The glycoside formation required mild conditions; it commenced with the reaction of the aglycone with the trichloroacetimidate donor to give a transient orthoester, which slowly rearranged to the desired aldgaropyranoside. The presence of the polar peripheral groups in the product did not impede the selective late-stage functionalization of the macrolide ring itself: the contained propargylic alcohol entity was readily transformed into the characteristic acyloin motif of the target by a ruthenium-catalyzed trans-hydrostannation followed by a modified Chan-Lam-type coupling.

SYNTHESIS OF 2-ALKYL-2,3-DIHYDRO-γ-PYRONES FROM 1-METHOXY-1-BUTEN-3-YNE

A method for the preparation of 2-alkyl-2,3-dihydro-γ-pyrones from 1-methoxy-1-buten-3-yne 1 and aliphatic aldehydes is reported.

Diels-Alder Reaction of Some Trimethylsilyloxy 1,3-Dienes

The thermal condensation of five trimethylsilyloxy 1,3-dienes with ethyl mesoxalate led to dihydropyran adducts.The trimethylsilyloxy radical was then removed by hydrolysis.The Danishefsky diene 1 was used to synthesize, with acetaldehyde, the 2,3-dihydro-2-methyl-4-pyrone (18), which was also obtained by two other independent ways.

Total Synthesis of Mycinamicin IV as Integral Part of a Collective Approach to Macrolide Antibiotics

The total synthesis of the 16-membered macrolide mycinamicin IV is outlined, which complements our previously disclosed, largely catalysis-based route to the aglycone. This work must also be seen in the context of our recent conquest of aldgamycin N, a related antibiotic featuring a similar core but a distinctly different functionalization pattern. Taken together, these projects prove that the underlying blueprint is integrative and hence qualifies for a collective approach to this prominent class of natural products. In both cases, the final glycosylation phase mandated close attention and was accomplished only after robust de novo syntheses of the (di)deoxy sugars of the desosamine, chalcose, mycinose and aldgarose types had been established. Systematic screening of the glycosidation promoter was also critically important for success.

HYDROXYL PURINE COMPOUNDS AND USE THEREOF

Disclosed are a series of hydroxyl purine compounds and the use thereof as PDE2 or TNFα inhibitors, in particular, the compounds as shown in formula (I), or tautomers or pharmaceutically acceptable salts thereof.

A Scalable Synthesis of (R,R)-2,6-Dimethyldihydro-2H-pyran-4(3H)-one

A scalable synthesis of (R,R)-2,6-dimethyldihydro-2H-pyran-4(3H)-one is reported. Key to this strategy is the Ti(OiPr)4-catalyzed Kulinkovich cyclopropanation of silyl protected (R)-ethyl 3-hydroxybutanoate, and subsequent oxidative fragmentati

HEPATITIS C VIRUS INHIBITORS

The present disclosure relates to compounds, compositions and methods for the treatment of hepatitis C virus (HCV) infection. Also disclosed are pharmaceutical compositions containing such compounds and methods for using these compounds in the treatment o

HEPATITIS C VIRUS INHIBITORS

The present disclosure relates to compounds of formula I, compositions and methods for the treatment of hepatitis C virus (HCV) infection. Also disclosed are pharmaceutical compositions containing such compounds and methods for using these compounds in th

NOVEL 4-(HETEROCYCLOALKYL)BENZENE-1,3-DIOL COMPOUNDS AS TYROSINASE INHIBITORS, PROCESS FOR THE PREPARATION THEREOF AND USE THEREOF IN HUMAN MEDICINE AND ALSO IN COSMETICS

The present invention relates to novel 4- (heterocycloalkyl) benzene- 1,3-diol compounds corresponding to general formula (I) below: to the compositions containing same, to the process for the preparation thereof and to the use thereof in pharmaceutical or cosmetic compositions for use in the treatment or prevention of pigmentary disorders

Routes for the synthesis of (2S)-2-methyltetrahydropyran-4-one from simple optically pure building blocks

Routes to (2S)-2-methyltetrahydropyran-4-one of high optical purity starting from readily available chiral pool precursors and suitable for large-scale manufacture are described. In one approach, the key step is cyclisation of (S)-5-hydroxyhex-1-en-3-one, derived either from an alkyl (S)-3-hydroxybutyrate or (S)-propylene oxide. Formation of the tetrahydropyran ring directly via an intramolecular oxy-Michael reaction under acid-catalysed conditions resulted in loss of optical purity, whereas proceeding through the intermediate (2S)-2-methyl-2,3-dihydropyran-4-one, via an oxidative Pd-catalysed ring closure, followed by hydrogenation of the alkenyl bond, preserved the optical purity. An alternative approach to (2S)-2-methyl-2,3-dihydropyran-4-one is also reported, again starting from an alkyl (S)-3-hydroxybutyrate by elaboration to a carbonyl-protected (6S)-6-methyl-5,6-dihydropyran-2,4-dione derivative, followed by partial reduction and dehydration. Alternatively, the carbonyl group can be reduced out completely in one step to furnish (2S)-2-methyltetrahydropyran-4-one directly after deprotection.