849905-14-2

Basic information

• Product Name: (R)-5-hydroxy-3-oxo-5-phenyl-pentanoic acid tert-butyl ester
• Synonyms: (R)-5-hydroxy-3-oxo-5-phenyl-pentanoic acid tert-butyl ester
• CAS NO: 849905-14-2
• Molecular Weight: 264.321
• Mol File: 849905-14-2.mol

Chemical Properties

• CAS DataBase Reference: (R)-5-hydroxy-3-oxo-5-phenyl-pentanoic acid tert-butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-5-hydroxy-3-oxo-5-phenyl-pentanoic acid tert-butyl ester(849905-14-2)
• EPA Substance Registry System: (R)-5-hydroxy-3-oxo-5-phenyl-pentanoic acid tert-butyl ester(849905-14-2)

Safety Data

• Hazardous Substances Data: 849905-14-2(Hazardous Substances Data)

Upstream product

• 58692-70-9 methyl (R)-3-hydroxy-3-phenylpropanoate 
• 1207973-75-8 lithium tert-butyl acetate 
• 540-88-5 acetic acid tert-butyl ester 
• 72656-47-4 ethyl (R)-3-hydroxy-3-phenylpropanoate 
• 98-86-2 acetophenone 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 100-52-7 benzaldehyde 
• 55848-87-8 t-butyl 5-hydroxy-3-oxo-5-phenylpentanoate 
• 1694-31-1 tert-butyl acetoacetate 

Relevant articles and documents

Revisiting the Maitland-Japp reaction. Concise construction of highly functionalised tetrahydropyran-4-ones

Application of modern synthetic methods to the Maitland-Japp reaction has provided a one pot, one step procedure for the efficient construction of highly substituted tetrahydropyran-4-ones. The Royal Society of Chemistry 2005.

A convenient stereoselective synthesis of 5-hydroxy-3-oxoesters and 3-hydroxy-5-oxoesters

A biocatalytic approach was employed for the asymmetric reduction of sterically demanding ketones to prepare 3-hydroxy-5-oxo-5-phenylpentanoates and 5-hydroxy-3-oxo-5-phenylpentanoates. Screening a collection of microorganisms led to the identification of

Asymmetric synthesis of (6R)-4-hydroxy-6-substituted-δ-lactones

A novel approach for the asymmetric synthesis of (6R)-4-hydroxy-6-substituted-δ-lactones has been achieved using asymmetric reduction of a prochiral ketone in the presence of (S)-(?)-diphenyl-prolinol/borane as a key step. The enantiomeric purity of the products was determined by chiral GC.

The one-pot, multi-component construction of highly substituted tetrahydropyran-4-ones using the Maitland-Japp reaction

A one-pot, multi-component reaction for the synthesis of highly substituted tetrahydropyran-4-ones, based on the long forgotten Maitland-Japp reaction has been realised. Two different aldehydes and a derivative of a β-ketoester can be condensed regioselectively in the presence of a Lewis acid to form tetrahydropyran-4-ones in excellent yields. The diastereoselectively of the reaction was found to be dependant upon the nature of the Lewis acid and the temperature at which the reaction was carried out. This procedure was also extended to the formation of tetrahydropyran-4-ones in greater than 95% enantiomeric excess. The Royal Society of Chemistry 2005.