69769-68-2

Basic information

• Product Name: (2S,3R,1'R)-Stegobinone
• Synonyms: (2S)-2,3-Dihydro-2β,3β,5-trimethyl-6-[(1R)-1-methyl-2-oxobutyl]-4H-pyran-4-one;(2S,3R,1'R)-Stegobinone
• CAS NO: 69769-68-2
• Molecular Formula: C13H20O3
• Molecular Weight: 224.2961
• Mol File: 69769-68-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (2S,3R,1'R)-Stegobinone(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3R,1'R)-Stegobinone(69769-68-2)
• EPA Substance Registry System: (2S,3R,1'R)-Stegobinone(69769-68-2)

Safety Data

• Hazardous Substances Data: 69769-68-2(Hazardous Substances Data)

Upstream product

• 72592-58-6 (S)-9-Hydroxy-4,6,8-trimethyl-decane-3,5,7-trione 
• 1187-04-8 4-methyl-3,5-heptanedione 
• 78522-78-8 (2S,3R)-2-methyl-3-tetrahydropyranyloxybutyric methylcarbonic anhydride 
• 72592-58-6 9-Hydroxy-4,6,8-trimethyl-decane-3,5,7-trione 
• 3720-38-5 (2S,3R)-3-Acetoxy-2-methylbutansaeure 
• 78522-79-9 (2S,3R)-2-methyl-3-tetrahydropyranyloxybutyric acid 
• 106022-40-6 (2S,3R)-6-((S)-2-Hydroxy-1-methyl-butyl)-2,3,5-trimethyl-2,3-dihydro-pyran-4-one 
• 78522-78-8 (2R,3S)-2-methyl-3-tetrahydropyranyloxybutyric methylcarbonic anhydride 
• 3720-38-5 (2R,3S)-3-Acetoxy-2-methyl-butyric acid 
• 78522-79-9 (2R,3S)-2-methyl-3-tetrahydropyranyloxybutyric acid 
• 108763-95-7 (2R)-3-t-butyldimethylsilyloxy-2-methylpentanoic acid 
• 372937-47-8 (2R)-3-t-butyldimethylsilyloxy-2-methylpentan-1-ol 
• 108763-93-5 (2R)-1-(1'-ethoxyethoxy)-2-methylpentan-3-ol 
• 152428-85-8 ((1S,2S,3S)-3-Benzyloxy-1,2-dimethyl-pentyloxy)-tert-butyl-dimethyl-silane 

Relevant articles and documents

Chemoenzymatic synthesis of stegobinone and stegobiol, components of the natural sex pheromone of the drugstore beetle (Stegobium paniceum L.)

NADPH-dependent ketoreductases were used for the chemoenzymatic stereoselective synthesis of the two componentsof the natural sex pheromone of the drugstore beetle. The key step in the asymmetric synthesis was the enzymatic reduction of an α-methyl-1,3-di

Synthesis of stegobiol and its oxidation to stegobinone, the components of the female-produced sex pheromone of the drugstore beetle

Crystalline (-)-stegobinone [(2S,3R,1′R)]-2,3-dihydro-2,3,5-trimethyl-6-(1′-methyl-2′- oxobutyl)-4H-pyran-4-one (1)], the major component of the female-produced sex pheromone of the drugstore beetle (Stegobium paniceum L.), was synthesized by oxidation of crystalline and the minor component (-)-stegobiol [(2S,3R,1′S,2′S)-2,3-dihydro-2,3,5-trimethyl-6-(2′-hydroxy- 1′-methylbutyl)-4H-pyran-4-one (2)] under the appropriate conditions using Jones's chromic acid, Dess-Martin's periodinane or Ley's ruthenium reagent. The latter (2) was synthesized by employing lipase and the Sharpless epoxidation for the introduction of the proper chiral centers. The streostructure of 1 was comfirmed by X-ray analysis.

A flexible stereocontrolled synthesis of β-hydroxy-α-methyl esters: Application to the synthesis of stegobiol and serricorole

β-Hydroxy-α-methyl esters have been obtained in a stereocontrolled manner and high enantiomeric and diastereomeric purity from commercially available methyl 3-oxopentanoate and methyl 3-oxobutanoate. The key step is file catalytic hydrogenation of the carbonyl group using (R)- or (S)-BINAP- Ru as chiral catalyst followed by asymmetric alkylation. Stegobiol and serricorole, components of the sex pheromone of the drugstore beetle, Stegobium paniceum (L.) and cigarette beetle, Lasioderma serricorne (F.), have been prepared from these chiral building blocks without the need for stoichiometric amounts of chiral auxiliaries.

Asymmetric synthesis of stegobinone via boronic ester chemistry

Highly stereoselective asymmetric boronic ester chemistry has been used to install all three chiral centers in a convergent synthesis of highly pure stegobinone, the epimerically labile pheromone of the drugstore beetle, Stegobium paniceum, and the furniture beetle, Anobium punctatum. Asymmetric centers were installed via the reaction of (dichloromethyl)lithium with 1,2-dicyclohexylethane- 1,2-diol boronic esters. The synthetic strategy utilizes a common (α-chloroalkyl)boronic ester intermediate as the source of both segments and all of the asymmetry of the target molecule. The two segments are joined by an aldol condensation and converted to stegobiol, a minor component of the S. paniceum pheromone and presumably the biogenetic precursor of stegobinone. Stegobiol is stable and easily purified, and is easily converted to pure stegobinone in a single oxidation step.

High-Precision Asymmetric Synthesis of Stegobiol and Stegobinone via Boronic Esters

Highly stereoselective boronic ester chemistry has been used to synthesize the drugstore beetle pheromones stegobiol and stegobinone.The convergent route utilizes a single intermediate containing all of the stereogenic centers for both segments of the phe

SYNTHESIS OF (2S,3R,1'R)-STEGOBINONE, THE PHEROMONE OF THE DRUGSTORE BEETLE, WITH STEREOCONTROL AT C-2 AND C-1'

(2S,3R,1'R)-Stegobinone , the pheromone of Stegobium paniceum L., was synthesized with stereocontrol at C-2 and C-1' starting from ethyl (R)-3-hydroxybutanoate and methyl (R)-3-hydroxy-

SYNTHESIS OF (2S,3R,7RS)-STEGOBINONE (2,3-DIHYDRO-2,3,5-TRIMETHYL-6-(1-METHYL-2-OXOBUTYL)-4H-PYRAN-4-ONE) AND ITS (2R,3S,7RS)-ISOMER. THE PHEROMONE OF THE DRUGSTORE BEETLE

Reaction of acetaldehyde with the trianion of 4,6-dimethylnonane-3,5,7-trione followed by acidification yielded a stereoisomeric mixture of stegobinone, the pheromone of Stegobium paniceum L.Acylation of the dianion derived from 4-methylheptane-3,5-dione