66901-50-6

Upstream product

• 950488-12-7 (S)-(-)-6-methylcyclohex-2-en-1-one 
• 102694-05-3 (2R,3R,6S)-6-methyl-2,3-epoxycyclohexan-1-one 
• 5524-05-0 (-)-dihydrocarvone 
• 108-24-7 acetic anhydride 
• 75276-18-5 (2S,5S)-5-(1-Hydroperoxy-1-methoxy-ethyl)-2-methyl-cyclohexanone 

Downstream Products

• 87086-66-6 trans-4-methyl-3- and 5-oxocyclohexyl acetate 
• 29569-75-3 (S)-1-Ethynyl-5-hydroxy-2-methyl-1-cyclohexene 
• 109243-43-8 (3R,6S)-6-methyl-3-<(tert-butyldimethylsilyl)oxy>cyclohexan-1-one 
• 109243-45-0 (2S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-1-[(1R,3aR,4S,7aR)-1-((R)-1,5-dimethyl-hexyl)-4-methoxy-7a-methyl-octahydro-inden-4-ylethynyl]-2-methyl-cyclohexanol 
• 109243-46-1 (3R,6S)-1-[(1R,3aR,4S,7aR)-1-((R)-1,5-Dimethyl-hexyl)-4-methoxy-7a-methyl-octahydro-inden-4-ylethynyl]-6-methyl-cyclohexane-1,3-diol 
• 109282-03-3 (3R,6S)-1-{(E)-2-[(1R,3aR,4R,7aR)-1-((R)-1,5-Dimethyl-hexyl)-4-methoxy-7a-methyl-octahydro-inden-4-yl]-vinyl}-6-methyl-cyclohexane-1,3-diol 
• 63162-93-6 (1R,4S)-3-[2-[(1R,3aS,7aR)-1-((R)-1,5-Dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(E)-ylidene]-4-methyl-cyclohexanol 
• 109361-34-4 (1R,4S)-3-[2-[(1R,3aS,7aR)-1-((R)-1,5-Dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-4-methyl-cyclohexanol 

Relevant academic research and scientific papers

Tunneling in tocopherol-mediated peroxidation of 7-dehydrocholesterol

The peroxidation of 7-dehydrocholesterol (7-DHC), a biosynthetic precursor to vitamin D3 and cholesterol, has been linked to the pathophysiology of Smith-Lemli-Optiz syndrome (SLOS), a devastating human disorder. In SLOS, 7-DHC plasma and tissue levels are elevated because of defects in the enzyme that convert it to cholesterol. α-Tocopherol can mediate the peroxidation of 7-DHC under certain circumstances and this prompted us to investigate the kinetic isotope effect (KIE) during this process. Thus, 9,14-d2-7-DHC was synthesized using a photochemical cyclization of deuterium-reinforced previtamin D3 (retro to its biosynthesis). Subsequently, we carried out co-oxidation of 9,14-h2-25,26,26,26,27,27,27-d7- and 9,14-d2-7-DHC in the presence of α-tocopherol under conditions that favor TMP. By monitoring the products formed from each precursor using mass spectrometry, the KIE for the hydrogen (deuterium) atom removal at C9 was found to be 21 ± 1. This large KIE value indicates that tunneling plays a role in the hydrogen atom transfer step in the tocopherol-mediated peroxidation of 7-DHC.

Total Synthesis of Dihydrovitamin DHV3 and Dihydrotachysterol DHT3. Application of the Low-Valent Titanium-Induced Reductive Elimination

Optically active ring A synthons 6, 11, 13, and 14, precursors of DHV3 and DHT3, were synthetized from (-)- and (+)-carvone.Application of the low-valent titanium-induced reductive elimination gave a new synthetic approach to vitamin D3 analogues, as show

CRIEGEE REARRANGEMENT OF α-ALKOXY HYDROPEROXIDES. A SYNTHESIS OF ESTERS AND LACTONES THAT COMPLEMENTS THE BAEYER-VILLIGER OXIDATION OF KETONES

α-Alkoxy hydroperoxides undergo Criegee rearrangement upon treatment with (CH3CO)2O to provide esters or lactones.