582321-42-4

Basic information

• Product Name: 6-Oxabicyclo[3.1.0]hexan-2-ol, 5-(2-methoxy-5-methylphenyl)-1-methyl-, 4-methylbenzenesulfonate, (1R,2R,5R)-
• CAS NO: 582321-42-4
• Molecular Formula: C21H24O5S
• Molecular Weight: 388.485
• Mol File: 582321-42-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 6-Oxabicyclo[3.1.0]hexan-2-ol, 5-(2-methoxy-5-methylphenyl)-1-methyl-, 4-methylbenzenesulfonate, (1R,2R,5R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Oxabicyclo[3.1.0]hexan-2-ol, 5-(2-methoxy-5-methylphenyl)-1-methyl-, 4-methylbenzenesulfonate, (1R,2R,5R)-(582321-42-4)
• EPA Substance Registry System: 6-Oxabicyclo[3.1.0]hexan-2-ol, 5-(2-methoxy-5-methylphenyl)-1-methyl-, 4-methylbenzenesulfonate, (1R,2R,5R)-(582321-42-4)

Safety Data

• Hazardous Substances Data: 582321-42-4(Hazardous Substances Data)

Upstream product

• 582321-39-9 3-(2-methoxy-5-methylphenyl)-2-methylcyclopent-2-en-1-one 
• 582321-40-2 (1R)-2-methyl-3-(2-methoxy-5-methyl)phenyl-2-cyclopenten-1-ol 
• 22117-97-1 3-isobutoxy-2-methyl-2-cyclopenten-1-one 
• 765-69-5 2-Methylcyclopentane-1,3-dione 
• 98-59-9 p-toluenesulfonyl chloride 
• 582321-41-3 (-)-(1R,2R,5R)-1-methyl-5-(2-methoxy-5-methyl)phenyl-6-oxabicyclo[3.1.0]hexan-2-ol 

Downstream Products

• 582321-44-6 (1R,2R)-1,2-dimethyl-2-(2-methoxy-5-methyl)phenyl-cyclopentanol 
• 81784-13-6 (1S)-1,2,2-trimethyl-1-(2-methoxy-5-methyl)phenylcyclopentane 
• 81784-10-3 4-methyl-2-[(1S)-1,2,2-trimethylcyclopentyl]phenol 
• 582321-43-5 (1R,3R)-3-methyl-3-(2-methoxy-5-methyl)phenyl-2-oxocyclopentyl 4-methylbenzenesulfonate 

Relevant articles and documents

The rearrangement of 2,3-epoxysulfonates and its application to natural products syntheses: Formal synthesis of (-)-aphanorphine and total syntheses of (-)-α-herbertenol and (-)-herbertenediol

The Lewis acid treatment of 2,3-epoxysulfonates with 2,3-dialkyl substituents or 2-alkyl-3-aryl substituents produced the rearrangement products via C3-cleavage of the oxirane ring in high yields. On the other hand, 2-aryl-3-alkyl-2,3-epoxysulfonates produced the products via C2-cleavage of the oxirane ring. The sulfonyloxy groups of the α-sulfonyloxy ketones, having a chiral benzylic quaternary carbon center obtained by the rearrangement of 2-alkyl-3-aryl-2,3-epoxysulfonates, were reductively eliminated to give the ketones with a chiral benzylic quaternary carbon center. The method was applied to the formal synthesis of (-)-aphanorphine and total syntheses of (-)-α-herbertenol and (-)-herbertenediol.