139137-98-7

Upstream product

• 2574-25-6 Diisopropyl chlorophosphate 
• 139137-97-6 2,2-Dimethyl-3-[(3E,7E,11E,15E,19E)-3,7,11,15,19-pentamethyl-21-(2,3,4,5-tetramethoxy-6-methyl-phenyl)-henicosa-3,7,11,15,19-pentaenyl]-oxirane 
• 118579-97-8 1-((2E,6E,10E,14E,18E)-3,7,11,15,19,23-Hexamethyl-tetracosa-2,6,10,14,18,22-hexaenyl)-2,3,4,5-tetramethoxy-6-methyl-benzene 
• 139137-96-5 diisopropyl <(4E)-1-isopropenyl-4-methyl-6-(2,3,4,5-tetramethoxy-6-methylphenyl)-4-hexenyl>phosphate 
• 85228-84-8 (E)-2,6-Dimethyl-8-(2,3,4,5-tetramethoxy-6-methyl-phenyl)-octa-1,6-dien-3-ol 
• 85228-79-1 1-<(2E)-6,7-epoxy-3,7-dimethyloct-2-enyl>-2,3,4,5-tetramethoxy-6-methylbenzene 
• 83036-57-1 (E)-1-(3,7-dimethylocta-2,6-dien-1-yl)-2,3,4,5-tetramethoxy-6-methylbenzene 

Downstream Products

• 303-98-0 2-((2E,6E,10E,14E,18E,22E,26E,30E,34E)-3,7,11,15,19,23,27,31,35,39-Decamethyl-tetraconta-2,6,10,14,18,22,26,30,34,38-decaenyl)-5,6-dimethoxy-3-methyl-[1,4]benzoquinone 
• 3066-88-4 1-((2E,6E,10E,14E,18E,22E,26E,30E,34E)-3,7,11,15,19,23,27,31,35,39-Decamethyl-tetraconta-2,6,10,14,18,22,26,30,34,38-decaenyl)-2,3,4,5-tetramethoxy-6-methyl-benzene 

Relevant academic research and scientific papers

Highly S(N)2'-, (E)-, and antiselective alkylation of allylic phosphates. Facile synthesis of coenzyme Q10

Treatment of secondary allylic chlorides or allylic phosphates in tetrahydrofuran with prenyl Grignard reagent in the presence of CuCN · 2 LiCl gave geraniol or farnesol derivatives with high S(N)2' selectivity. Phosphate leaving groups were highly transstereoselective for the formation of (E,E)-farnesol derivatives. Furthermore, complete anti-S(N)2' selectivity was observed in the alkylation of optically active allylic phosphates. The present method appears to be an excellent carbon-carbon coupling reaction with high regio-, (E)-, and enantioselectivity. Coenzyme Q10 (ubiquinone 10) was efficiently synthesized using this methodology.