2857-75-2

Basic information

• Product Name: (R)-5-Methyltetrahydro-2H-pyran-2-one
• Synonyms: (R)-5-Methyltetrahydro-2H-pyran-2-one;(5R)-Tetrahydro-5-Methyl-2H-pyran-2-one;(5R)-5-methyloxan-2-one
• CAS NO: 2857-75-2
• Molecular Formula: C₆H₁₀O₂
• Molecular Weight: 114.1424
• Mol File: 2857-75-2.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 60-62℃ (2 Torr)
• Appearance: /
• Storage Temp.: Refrigerator, under inert atmosphere
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: (R)-5-Methyltetrahydro-2H-pyran-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-5-Methyltetrahydro-2H-pyran-2-one(2857-75-2)
• EPA Substance Registry System: (R)-5-Methyltetrahydro-2H-pyran-2-one(2857-75-2)

Safety Data

• Hazardous Substances Data: 2857-75-2(Hazardous Substances Data)

Usage

Uses

(5R)-Tetrahydro-5-methyl-2H-pyran-2-one, can be used as an intermediate in the synthesis of many pharmaceutical compounds. It is used in the synthesis of (-)-Englerin A, a potent and selective inhibitor of renal cancer cell lines.

Upstream product

• 159811-80-0 1-(2-methylpropyl) 5-hydrogen (R)-2-methylpentanedioate 
• 6672-30-6 (R)-3-methylcyclopentanone 
• 512-04-9 diosgenin 
• 31468-33-4 2-methylglutaric anhydride 
• 545-77-7 3β,12β-dihydroxy-(25R)-5α-spirostane 
• 1757-42-2 3-methyl-cyclopentanone 
• 77-60-1 tigogenin 
• 159684-81-8 1-(2-methylpropyl) 5-hydrogen (+/-)-2-methylpentanedioate 
• 869291-81-6 (4R)-4,8-dimethylnonane-2,7-dione 

Downstream Products

• 1115-81-7 (R)-2-methylglutaric acid 
• 909879-22-7 methyl (R)-5-bromo-4-methylpentanoate 
• 1394045-10-3 (R,E)-ethyl 2,6-dimethyl-7-(tosyloxy)hept-2-enoate 
• 1394045-11-4 (R,E)-7-hydroxy-2,6-dimethylhept-5-enyl 4-methylbenzenesulfonate 
• 1394045-13-6 (S)-2-(methoxymethoxy)-2-((1R,2R,3R)-3-methyl-2-vinylcyclopentyl)propan-1-ol 
• 156767-44-1 (+)-(R)-2-Methyl-5-phenyl-1-pentanol 
• 156767-45-2 (2R)-2-methyl-5-phenylpentan-1-al 
• 156661-61-9 (-)-(R)-6-Methyl-9-phenyl-(E)-4-nonenoic acid ethyl ester 

Relevant articles and documents

Biocatalytic Characterization of Human FMO5: Unearthing Baeyer-Villiger Reactions in Humans

Flavin-containing mono-oxygenases are known as potent drug-metabolizing enzymes, providing complementary functions to the well-investigated cytochrome P450 mono-oxygenases. While human FMO isoforms are typically involved in the oxidation of soft nucleophiles, the biocatalytic activity of human FMO5 (along its physiological role) has long remained unexplored. In this study, we demonstrate the atypical in vitro activity of human FMO5 as a Baeyer-Villiger mono-oxygenase on a broad range of substrates, revealing the first example to date of a human protein catalyzing such reactions. The isolated and purified protein was active on diverse carbonyl compounds, whereas soft nucleophiles were mostly non- or poorly reactive. The absence of the typical characteristic sequence motifs sets human FMO5 apart from all characterized Baeyer-Villiger mono-oxygenases so far. These findings open new perspectives in human oxidative metabolism.

Production process for 16-dehydropregnenoneol and its analogs

The present invention relates to a clean process for the degradation of steroidal sapogenin to produce 16-dehydropregnenolone and its analogs. The pure or the crude pseudo steroidal sapogenin, derived from steroidal sapogenin, dissolved in organic solvent, reacts with hydrogen peroxide with or without metal compound and acid as catalyst, and the crude products directly go through elimination and hydrolization in the presence of base to give 16-Dehydropregnenolone or its analog, accompanied with the other product 4R(or S)-methyl-5-hydroxy-pentate, which is converted to 4R(or S)-methyl-δ-pentyl lactone after acidification and extraction from the water layer. This technology improved the utilizing degree of steroidal sapogenin, improved the yield, and cleared up the chromium pollution in the former technique. In a word, the method disclosed in this invention is more suitable for manufacture.

Novel synthesis of (4R)-4-methylpentanolide from (L)-(-)-menthol

A novel synthesis of the promising optically pure chiral (4R)-4-methylpentanolide that is based on several regiospecific oxidative transformations of (4R)-2,4-dimethyl-1-(1-methylethyl)-1-cyclohexene, the product of addition of (-)-menthone and methylmagn