446246-12-4

Basic information

• Product Name: (1R,2S,6R,7S)-5-[(1R,2S)-2-hydroxy-3,3-dimethyl-1-(phenylsulfanyl)butyl]-1,10,10-trimethyl-3-oxa-5-azatricyclo[5.2.1.0^2,6]decan-4-one
• Synonyms: (1R,2S,6R,7S)-5-[(1R,2S)-2-hydroxy-3,3-dimethyl-1-(phenylsulfanyl)butyl]-1,10,10-trimethyl-3-oxa-5-azatricyclo[5.2.1.0^2,6]decan-4-one
• CAS NO: 446246-12-4
• Molecular Weight: 403.586
• Mol File: 446246-12-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (1R,2S,6R,7S)-5-[(1R,2S)-2-hydroxy-3,3-dimethyl-1-(phenylsulfanyl)butyl]-1,10,10-trimethyl-3-oxa-5-azatricyclo[5.2.1.0^2,6]decan-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2S,6R,7S)-5-[(1R,2S)-2-hydroxy-3,3-dimethyl-1-(phenylsulfanyl)butyl]-1,10,10-trimethyl-3-oxa-5-azatricyclo[5.2.1.0^2,6]decan-4-one(446246-12-4)
• EPA Substance Registry System: (1R,2S,6R,7S)-5-[(1R,2S)-2-hydroxy-3,3-dimethyl-1-(phenylsulfanyl)butyl]-1,10,10-trimethyl-3-oxa-5-azatricyclo[5.2.1.0^2,6]decan-4-one(446246-12-4)

Safety Data

• Hazardous Substances Data: 446246-12-4(Hazardous Substances Data)

Upstream product

• 7205-91-6 phenylthiomethyl chloride 
• 108-98-5 thiophenol 
• 446246-10-2 (1R,2S,6R,7S)-5-[(1R,2R)-2-hydroxy-2-cyclohexyl-1-(phenylsulfanyl)ethyl]-1,10,10-trimethyl-3-oxa-5-azatricyclo[5.2.1.0^2,6]decan-4-one 
• 446246-14-6 (1R,2S,6R,7S)-1,10,10-trimethyl-5-[(1R)-2-oxo-2-cyclohexyl-1-(phenylsulfanyl)ethyl]-3-oxa-5-azatricyclo[5.2.1.0^2,6]decan-4-one 
• 446246-09-9 (1R,2S,6R,7S)-5-[(1R,2R)-2-hydroxy-2-phenyl-1-(phenylsulfanyl)ethyl]-1,10,10-trimethyl-3-oxa-5-azatricyclo[5.2.1.0^2,6]decan-4-one 
• 446246-13-5 (1R,2S,6R,7S)-1,10,10-trimethyl-5-[(1R)-2-oxo-2-phenyl-1-(phenylsulfanyl)ethyl]-3-oxa-5-azatricyclo[5.2.1.0^2,6]decan-4-one 
• 446246-08-8 (1R,2S,6R,7S)-1,10,10-trimethyl-5-phenylsulfanylmethyl-3-oxa-5-azatricyclo[5.2.1.0^2,6]decan-4-one 
• 41719-63-5 (1R,2S,6R,7S)-(-)-1,10,10-trimethyl-3-oxa-5-azatricyclo[5.2.1.0^2,6]decan-4-one 
• 446246-15-7 (1R,2S,6R,7S)-1,10,10-trimethyl-5-[(1R)-2-oxo-3,3-dimethyl-1-(phenylsulfanyl)butyl]-3-oxa-5-azatricyclo[5.2.1.0^2,6]decan-4-one 
• 630-19-3 pivalaldehyde 

Downstream Products

• 21641-92-9 (S)-2-hydroxy-3,3-dimethylbutanoic acid 
• 446246-08-8 (1R,2S,6R,7S)-1,10,10-trimethyl-5-phenylsulfanylmethyl-3-oxa-5-azatricyclo[5.2.1.0^2,6]decan-4-one 
• 446246-09-9 (1R,2S,6R,7S)-5-[(1R,2R)-2-hydroxy-2-phenyl-1-(phenylsulfanyl)ethyl]-1,10,10-trimethyl-3-oxa-5-azatricyclo[5.2.1.0^2,6]decan-4-one 
• 446246-10-2 (1R,2S,6R,7S)-5-[(1R,2R)-2-hydroxy-2-cyclohexyl-1-(phenylsulfanyl)ethyl]-1,10,10-trimethyl-3-oxa-5-azatricyclo[5.2.1.0^2,6]decan-4-one 

Relevant articles and documents

Lithiated camphor-derived oxazolidinone S,N-acetals as chiral formyl anion synthons in additions to aldehydes. Asymmetric synthesis of α-hydroxy aldehydes and α-hydroxy acids

N-(Phenylthiomethyl)oxazolidinones derived from camphor can be lithiated and added to aldehydes in good yields and stereoselectivities. The adducts are crystalline, which simplifies isolation of the major diastereomer from the product mixture. Hydrolysis affords enantiopure α-hydroxy aldehydes, which can be oxidized to α-hydroxy acids in good yields. The steric course of the reaction is analyzed in detail and a mechanistic model is presented.