65817-46-1

Basic information

• Product Name: (2S,7S,8S)-sarcophytoxide
• CAS NO: 65817-46-1
• Molecular Weight: 302.457
• Mol File: 65817-46-1.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (2S,7S,8S)-sarcophytoxide(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,7S,8S)-sarcophytoxide(65817-46-1)
• EPA Substance Registry System: (2S,7S,8S)-sarcophytoxide(65817-46-1)

Safety Data

• Hazardous Substances Data: 65817-46-1(Hazardous Substances Data)

Upstream product

• 70645-54-4 (-)-sarcophytonin A 
• 1042909-29-4 C₂₀H₃₁ClO₂ 
• 1042909-28-3 C₂₀H₃₁ClO₂ 
• 1043616-74-5 C₂₀H₃₂O₃ 

Downstream Products

• 55038-27-2 Sarcophine 
• 74740-97-9 (2E,11E)-(6S,8S)-3,8,12,16-Tetramethyl-7,18-dioxa-tricyclo[13.3.0.0^6,8]octadeca-1⁽¹⁵⁾,2,11,16-tetraene 
• 137762-26-6 (1E,11E)-(6S,8S)-3-Hydroxy-3,8,12,16-tetramethyl-7,18-dioxa-tricyclo[13.3.0.0^6,8]octadeca-1,11,15-trien-17-one 
• 137762-25-5 (1E,11E)-(6S,8S)-3-Hydroperoxy-3,8,12,16-tetramethyl-7,18-dioxa-tricyclo[13.3.0.0^6,8]octadeca-1,11,15-trien-17-one 

Relevant articles and documents

Acid-catalyzed reactions of sarcophytoxide, a marine cembranoid: An apparently enantio-directive reaction, unusual products and stereochemical reconsideration of epoxide-ketone rearrangement

Perchloric acid treatment of sarcophytoxide, a marine cembranoid possessing an epoxide, brought about epoxide ketone rearrangement affording ketones. When the reaction time was long (22 h), a minor ketone that was antipodal to the ketone obtained in a short-time (l0min) reaction was formed. These puzzling findings, considering that the starting epoxide had three asymmetric carbons, were interpreted by surveying the structures of other ketonic products. The stereochemistry of a major ketone, which had been wrongly assigned, was corrected by extensive analyses of NMR spectra. The correct stereochemistry indicated that the epoxide-ketone rearrangement took a course via a cationic intermediate.