82110-22-3

Basic information

• Product Name: (R)-2-Methyltetrahydropyran-4-one
• Synonyms: (R)-2-Methyltetrahydropyran-4-one;(2R)-2-Methyltetrahydropyran-4-one;(2R)-2-methyloxan-4-one;(R)-2-Methyldihydro-2H-pyran-4(3H)-one;(R)-2-methyltetrahydro-4H-pyran-4-one;EOS-62012;4H-Pyran-4-one, tetrahydro-2-methyl-, (2R)-
• CAS NO: 82110-22-3
• Molecular Formula: C₆H₁₀O₂
• Molecular Weight: 114.1424
• Mol File: 82110-22-3.mol

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: (R)-2-Methyltetrahydropyran-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-2-Methyltetrahydropyran-4-one(82110-22-3)
• EPA Substance Registry System: (R)-2-Methyltetrahydropyran-4-one(82110-22-3)

Safety Data

• Hazardous Substances Data: 82110-22-3(Hazardous Substances Data)

Usage

Uses

Used in the Fragrance Industry:
(R)-2-Methyltetrahydropyran-4-one is used as a fragrance ingredient for its sweet, creamy, and caramel-like scent. It adds depth and complexity to perfumes and personal care products, enhancing the overall sensory experience for consumers.
Used in the Flavoring Industry:
As a flavoring agent, (R)-2-Methyltetrahydropyran-4-one is utilized in the food and beverage sector to impart a rich, caramel-like flavor to products, contributing to a more enjoyable and satisfying taste.
Used in Green Chemistry:
(R)-2-Methyltetrahydropyran-4-one is studied for its potential as a renewable and sustainable alternative to petroleum-derived chemicals. This makes it a subject of interest in the field of green chemistry, where the development of eco-friendly and sustainable chemical processes is a priority.

Upstream product

• 89791-47-9 (2S,4S)-4-hydroxy-2-methyltetrahydropyran 
• 1193-20-0 2-methyltetrahydro-4H-pyran-4-one 
• 67-63-0 isopropyl alcohol 
• 190912-17-5 (R)-2-methyl-2,3-dihydro-4H-pyran-4-one 
• 869293-25-4 (R)-5-((tert-butyldimethylsilyl)oxy)hex-1-en-3-one 
• 548440-36-4 (S)-5-((tert-butyldimethylsilyl)oxy)hex-1-en-3-one 
• 33747-08-9 cis-2-methyltetrahydro-2H-pyran-4-ol 
• 33747-08-9 (2R,4R)-2-methyltetrahydro-2H-pyran-4-ol 

Downstream Products

• 146565-12-0 (2R,4R)-4-(3-Benzyloxy-5-fluoro-phenyl)-4-methoxy-2-methyl-tetrahydro-pyran 
• 146608-99-3 (2R,4S)-4-(3-Benzyloxy-5-fluoro-phenyl)-4-methoxy-2-methyl-tetrahydro-pyran 
• 146502-48-9 (2R,4S)-4-(3-Benzyloxy-5-fluoro-phenyl)-2-methyl-tetrahydro-pyran-4-ol 
• 146565-09-5 (2R,4R)-4-(3-Benzyloxy-5-fluoro-phenyl)-2-methyl-tetrahydro-pyran-4-ol 

Relevant articles and documents

Ketoreductase/Transaminase, One-Pot, Multikilogram Biocatalytic Cascade Reaction

A biocatalytic cascade to produce tert-butyl ((2R,4R)-2-methyltetrahydro-2H-pyran-4-yl)carbamate 6 has been demonstrated at the multikilogram scale. In this reaction, a racemic ketone is resolved by reducing the undesired ketone using a ketone reductase (KRED). The reduction is stereospecific for the 2-position of substrate (2S)-ketone leaving the (2R)-ketone unreacted. After the (2S)-ketone has been depleted, a transaminase is added to catalyze the enantioselective transamination of the ketone, resulting in formation of the (2R, 4R)-amine 6. The product is recovered from the aqueous reaction after Boc protection.

Discovery of MK-6169, a Potent Pan-Genotype Hepatitis C Virus NS5A Inhibitor with Optimized Activity against Common Resistance-Associated Substitutions

We describe the discovery of MK-6169, a potent and pan-genotype hepatitis C virus NS5A inhibitor with optimized activity against common resistance-associated substitutions. SAR studies around the combination of changes to both the valine and aminal carbon region of elbasvir led to the discovery of a series of compounds with substantially improved potency against common resistance-associated substitutions in the major genotypes, as well as good pharmacokinetics in both rat and dog. Through further optimization of key leads from this effort, MK-6169 (21) was discovered as a preclinical candidate for further development.

Novel Imidazo[4,5-c]Quinoline And Imidazo[4,5-c][1,5]Naphthyridine Derivatives As LRRK2 Inhibitors

The present invention provides novel imidazo[4,5-c]quinoline and imidazo[4,5-c][1,5]naphthyridine derivatives of Formula (I), and the pharmaceutically acceptable salts thereof wherein R1, R1a, R1b, R2, R4, R5, R6, X and Z are as defined in the specification. The invention is also directed to pharmaceutical compositions comprising the compounds of Formula (I) and to use of the compounds in the treatment of diseases associated with LRRK2, such as neurodegenerative diseases including Parkinson's disease or Alzheimer's disease, cancer, Crohn's disease or leprosy.

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

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.

Enzymes in Organic Synthesis. 25. Heterocyclic Ketones as Substrates of Horse Liver Alcohol Dehydrogenase. Highly Stereoselective Reductions of 2-Substituted Tetrahydropyran-4-ones

Horse liver alcohol dehydrogenase (HLADH) has been found to be an efficient catalyst for the reduction of O-heterocyclic ketones.Preparative-scale HLADH-catalyzed reductions of 2-substituted tetrahydropyran-4-ones are enantioselective, with reduction of e