153080-60-5

Basic information

• Product Name: l-menthyl (2R,6S)-6-methyl-4-oxo-2-phenyl-1,3-dioxane-2-carboxylate
• Synonyms: l-menthyl (2R,6S)-6-methyl-4-oxo-2-phenyl-1,3-dioxane-2-carboxylate
• CAS NO: 153080-60-5
• Molecular Weight: 374.477
• Mol File: 153080-60-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: l-menthyl (2R,6S)-6-methyl-4-oxo-2-phenyl-1,3-dioxane-2-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: l-menthyl (2R,6S)-6-methyl-4-oxo-2-phenyl-1,3-dioxane-2-carboxylate(153080-60-5)
• EPA Substance Registry System: l-menthyl (2R,6S)-6-methyl-4-oxo-2-phenyl-1,3-dioxane-2-carboxylate(153080-60-5)

Safety Data

• Hazardous Substances Data: 153080-60-5(Hazardous Substances Data)

Upstream product

• 20229-41-8 l-menthyl phenylglyoxylate 
• 75-16-1 methylmagnesium bromide 
• 153080-59-2 l-menthyl (R)-2-phenyl-4-oxo-1,3-dioxine-2-carboxylate 

Downstream Products

• 53562-86-0 (S)-3-hydroxybutyric acid methyl ester 

Relevant articles and documents

l-Menthyl (R)-2-phenyl-4-oxo-1,3-dioxine-2-carboxylate: Diastereofacial selectivity for conjugate addition and its explanation

l-Menthyl (R)- and (S)-2-phenyl-4-oxo-1,3-dioxine-2-carboxylates are synthesized from l-menthyl phenylglyoxylate by reacting with formylketene followed by fractional crystallization. Conjugate addition to the (R)-2-phenyl-4-oxo-1,3-dioxine-2-carboxylate by RMgBr/CuI has revealed that the reagent attacks from the phenyl side which takes the quasi-equatorial orientation in the sofa comformation of the dioxinone ring with complete diastereoselection. This finding is contrast to the reverse diastereoselectivity in the same reaction of 2-tert-butyl-6-methyl-1,3-dioxin-4-one and its 2-methyl derivative. A possible reason to account for this difference is proposed.