131149-29-6

Basic information

• Product Name: (2R,3S)-2-Hydroxy-5-phenylselanyl-4-((E)-propenyl)-3-(2-trimethylsilanyl-ethoxy)-cyclopentanone
• CAS NO: 131149-29-6
• Molecular Weight: 411.475
• Mol File: 131149-29-6.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (2R,3S)-2-Hydroxy-5-phenylselanyl-4-((E)-propenyl)-3-(2-trimethylsilanyl-ethoxy)-cyclopentanone(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3S)-2-Hydroxy-5-phenylselanyl-4-((E)-propenyl)-3-(2-trimethylsilanyl-ethoxy)-cyclopentanone(131149-29-6)
• EPA Substance Registry System: (2R,3S)-2-Hydroxy-5-phenylselanyl-4-((E)-propenyl)-3-(2-trimethylsilanyl-ethoxy)-cyclopentanone(131149-29-6)

Safety Data

• Hazardous Substances Data: 131149-29-6(Hazardous Substances Data)

Upstream product

• 6386-72-7 (E)-propenyl lithium 
• 131233-96-0 (4R,5S)-5-Hydroxy-2-phenylselanyl-4-(2-trimethylsilanyl-ethoxy)-cyclopent-2-enone 
• 131149-28-5 (+/-)-trans-2-benzeneselenenyl-5-hydroxy-4-(2-trimethylsilylethoxy)-2-cyclopenten-1-one 
• 126566-35-6 6-(2-trimethylsilylethoxy)-2,3-dihydro-6H-pyran-3-one 
• 126566-40-3 trans-5-hydroxy-4-(2-trimethylsilylethoxy)-2-cyclopenten-1-one 
• 34837-55-3 Phenylselenyl bromide 
• 131233-94-8 (1S,4R)-4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid (1S,5R)-2-oxo-5-(2-trimethylsilanyl-ethoxy)-cyclopent-3-enyl ester 
• 131233-95-9 (-)-(4R,5S)-5-hydroxy-4-(2-trimethylsilylethoxy)-2-cyclopenten-1-one 

Downstream Products

• 582-46-7 (+)-terrein 
• 582-46-7 (+/-)-terrein 

Relevant articles and documents

A total synthesis of racemic and optically active terrein (trans-4,5-dihydroxy-3-[(E)-1-propenyl]-2-cyclopenten-1-one)

Two routes to terrein (1), employing a novel ring contraction of 6-alkoxy-2,3-dihydro-6H-pyran-3-ones (5, 13) are described. Separation into enantiomers was carried out by classical resolution via diastereomeric camphanic acid ester intermediates (14, 15)