144318-32-1

Basic information

• Product Name: N-{2-[(5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-6-hydroxy-cyclohex-1-enyl]-ethyl}-4,N-dimethyl-benzenesulfonamide
• Synonyms: N-{2-[(5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-6-hydroxy-cyclohex-1-enyl]-ethyl}-4,N-dimethyl-benzenesulfonamide
• CAS NO: 144318-32-1
• Molecular Weight: 439.692
• Mol File: 144318-32-1.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: N-{2-[(5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-6-hydroxy-cyclohex-1-enyl]-ethyl}-4,N-dimethyl-benzenesulfonamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-{2-[(5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-6-hydroxy-cyclohex-1-enyl]-ethyl}-4,N-dimethyl-benzenesulfonamide(144318-32-1)
• EPA Substance Registry System: N-{2-[(5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-6-hydroxy-cyclohex-1-enyl]-ethyl}-4,N-dimethyl-benzenesulfonamide(144318-32-1)

Safety Data

• Hazardous Substances Data: 144318-32-1(Hazardous Substances Data)

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 144318-25-2 4,N-Dimethyl-N-[2-(3-oxo-cyclohex-1-enyl)-ethyl]-benzenesulfonamide 
• 144318-24-1 4-Methyl-N-[2-(3-oxo-cyclohex-1-enyl)-ethyl]-benzenesulfonamide 
• 144318-26-3 N-[2-(3-Hydroxy-cyclohex-1-enyl)-ethyl]-4,N-dimethyl-benzenesulfonamide 
• 144318-27-4 N-[2-((1S,5S,6S)-5-Hydroxy-7-oxa-bicyclo[4.1.0]hept-1-yl)-ethyl]-4,N-dimethyl-benzenesulfonamide 
• 61273-80-1 2-(5-methoxy-cyclohexa-1,4-dienyl)-ethylamine 
• 69739-34-0 t-butyldimethylsiyl triflate 
• 144318-28-5 N-[2-((5R,6S)-5,6-Dihydroxy-cyclohex-1-enyl)-ethyl]-4,N-dimethyl-benzenesulfonamide 

Downstream Products

• 125-28-0 (+/-)-dihydroisocodeine 
• 125-28-0 (+/-)-dihydrocodeine 
• 144318-22-9 N-(2-{(5S,6S)-6-[2-Bromo-6-methoxy-3-((E)-2-phenylsulfanyl-vinyl)-phenoxy]-5-hydroxy-cyclohex-1-enyl}-ethyl)-4,N-dimethyl-benzenesulfonamide 
• 144318-23-0 N-[2-((3R,3aR,9aS,9bS)-3-Hydroxy-5-methoxy-1,3,3a,9a-tetrahydro-2H-phenanthro[4,5-bcd]furan-9b-yl)-ethyl]-4,N-dimethyl-benzenesulfonamide 
• 144318-25-2 4,N-Dimethyl-N-[2-(3-oxo-cyclohex-1-enyl)-ethyl]-benzenesulfonamide 
• 144318-28-5 N-[2-((5R,6S)-5,6-Dihydroxy-cyclohex-1-enyl)-ethyl]-4,N-dimethyl-benzenesulfonamide 
• 144318-26-3 N-[2-(3-Hydroxy-cyclohex-1-enyl)-ethyl]-4,N-dimethyl-benzenesulfonamide 
• 144318-27-4 N-[2-((1S,5S,6S)-5-Hydroxy-7-oxa-bicyclo[4.1.0]hept-1-yl)-ethyl]-4,N-dimethyl-benzenesulfonamide 
• 144318-30-9 N-{2-[(5R,6R)-6-[2-Bromo-6-methoxy-3-((E)-2-phenylsulfanyl-vinyl)-phenoxy]-5-(tert-butyl-dimethyl-silanyloxy)-cyclohex-1-enyl]-ethyl}-4,N-dimethyl-benzenesulfonamide 

Relevant articles and documents

Enantioselective synthesis of (-)-dihydrocodeinone: A short formal synthesis of (-)-morphine

The radical cyclization approach to the morphine alkaloids has been applied in an asymmetric synthesis of (-)-dihydrocodeinone. A chiral cyclohexenol (R-32), from the CBS reduction of the enone, is the source of chirality. The first key step, tandem closure in which stereochemistry is controlled by geometric constraints, (-)-15b → (+)-16, was followed by an unprecedented reductive hydroamination, completing the synthesis of (-)-dihydroisocodeine ((-)-17) in 13 steps from commercially available materials.