112571-15-0

Basic information

• Product Name: (2S,3S,1'R)-stegobinone
• CAS NO: 112571-15-0
• Molecular Weight: 224.3
• Mol File: 112571-15-0.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: (2S,3S,1'R)-stegobinone(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3S,1'R)-stegobinone(112571-15-0)
• EPA Substance Registry System: (2S,3S,1'R)-stegobinone(112571-15-0)

Safety Data

• Hazardous Substances Data: 112571-15-0(Hazardous Substances Data)

Upstream product

• 106022-40-6 (2S,3R)-6-((S)-2-Hydroxy-1-methyl-butyl)-2,3,5-trimethyl-2,3-dihydro-pyran-4-one 
• 72592-58-6 (S)-9-Hydroxy-4,6,8-trimethyl-decane-3,5,7-trione 
• 106022-40-6 (2S,3R)-2,3-dihydro-6-[(1'S,2'S)-2'-hydroxy-1'-methylbutyl]-2,3,5-trimethyl-4H-pyran-4-one 
• 1576-96-1 (E)-2-penten-1-ol 
• 6261-22-9 pent-2-yn-1-ol 
• 104530-72-5 ((2S,3S)-3-ethyloxiran-2-yl)methanol 
• 108779-16-4 (2S,3S)-3-tert-butyldimethylsilyloxy-2-methylpentanoic acid 
• 108815-14-1 (1'S,2'R)-1',2'-dimethyl-3'-oxopentyl (2S,3S)-3-tert-butyldimethylsilyloxy-2-methylpentanoate 
• 80632-79-7 (2R,3S)-3-t-butyldimethylsilyloxy-2-methylpentan-1-ol 
• 208766-56-7 (2R,3S)-2-methylpentane-1,3-diol 
• 208766-66-9 (2S,3R)-6-[(1S,2S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-butyl]-2,3,5-trimethyl-2,3-dihydro-pyran-4-one 
• 208766-59-0 2,2-Dimethyl-propionic acid (2R,3S)-3-hydroxy-2-methyl-pentyl ester 
• 208766-61-4 2,2-Dimethyl-propionic acid (2R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-pentyl ester 
• 208766-51-2 ((2S,3S)-3-ethyloxiran-2-yl)methyl 4-nitrobenzoate 

Relevant articles and documents

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.

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