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
• Article Data: 7

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

General Description

(R)-2-Methyltetrahydropyran-4-one, also known as S(-)-2-Methyltetrahydropyran-4-one, is a chemical compound with the molecular formula C6H10O2. It is a colorless liquid with a sweet, creamy, caramel-like odor, and is commonly used in the fragrance and flavoring industry. (R)-2-Methyltetrahydropyran-4-one is often found in natural products, and is used as a flavoring agent in foods and beverages. It is also used as a fragrance ingredient in perfumes and personal care products. Additionally, (R)-2-Methyltetrahydropyran-4-one has been studied for its potential as a renewable and sustainable alternative to petroleum-derived chemicals, making it a subject of interest in the field of green chemistry.

Upstream product

• 89791-47-9 (2S,4S)-4-hydroxy-2-methyltetrahydropyran 
• 548440-36-4 (S)-5-((tert-butyldimethylsilyl)oxy)hex-1-en-3-one 
• 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 
• 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.

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.

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.