73875-21-5

Upstream product

• 59277-17-7 1-(benzenesulfonyl)-2-methyl-4-chloro-2-butene 
• 73875-27-1 2,3,4,5-tetramethoxy-6-methyl-1-bromobenzene 
• 5829-79-8 (E)-4-chloro-2-methyl-1-phenylsulfonyl-2-butene 
• 35896-58-3 2,3,4,5-tetramethoxytoluene 
• 53588-16-2 (E)-4-hydroxy-2-methyl-1-phenylsulfonyl-2-butene 
• 98-09-9 benzenesulfonyl chloride 
• 78-79-5 isoprene 

Downstream Products

• 303-98-0 ubidecarenone 
• 1092067-54-3 (E)-6-[4-(benzenesulfonyl)-3-methylbut-2-enyl]-2,3-dimethoxy-5-methylbenzene-1,4-diol 
• 73875-22-6 (E)-1-(benzenesulfonyl)-4-[3,4-dimethoxy-2,5-bis(methoxymethoxy)-6-methylphenyl]-2-methylbut-2-ene 
• 74813-93-7 4-(benzenesulfonyl)-3,7,11,15,19,23,27,31,35,39-decamethyl-1-[3,4-dimethoxy-2,5-bis(methoxymethoxy)-6-methylphenyl]tetraconta-2,6,10,14,18,22,26,30,34,38-decaene 
• 64634-91-9 1-[(2E,6E,10E,14E,18E,22E,26E,30E,34E)-3,7,11,15,19,23,27,31,35,39-decamethyltetraconta-2,6,10,14,18,22,26,30,34,38-decaen-1-yl]-3,4-dimethoxy-2,5-bis(methoxymethoxy)-6-methylbenzene 
• 618457-07-1 (2'E,6'E,10'E,14'E,18'E,22'E,26'E,30'E,34'E,38'E)-1-(3,7',11',15',19',23',27',31',35',39'-decamethyl-4'-phenylsulfonyltetraconta-2',6',10',14',18',22',26',30',34',38'-decaenyl)-6-methyl-2,3,4,5-tetramethoxybenzene 

Relevant academic research and scientific papers

Synthesis of coenzyme Q10

A practical synthesis of coenzyme Q10 has been developed. The route features an improved Friedel-Crafts allylation of tetramethoxytoluene with a para-chlorobenzenesulfonyl-substituted C5 allylic chloride at 40 °C. Replacement of the methyl ether protecting groups of the para-hydroquinone by methoxymethyl groups at Q1 stage proceeded efficiently, and allowed the facile final oxidation to coenzyme Q10 to occur under mild acidic conditions. The overall yield of coenzyme Q 10 from commercially available tetramethoxytoluene reached 53 % in this improved procedure. An improved synthesis gave CoQ10 in 53 % overall yield from tetramethoxytoluene through Friedel-Crafts allylation with a para-chlorobenzenesulfonyl-substituted C5 allylic chloride and a modified oxidation procedure. Copyright

The Friedel-Crafts allylation of a prenyl group stabilized by a sulfone moiety: Expeditious syntheses of ubiquinones and menaquinones

An efficient synthetic method for the protected p-hydroquinone compounds 4 containing the C5 trans allylic sulfone moiety has been developed by the direct Friedel-Crafts allylation of the protected dihydroquinone 2 with 4-chloro-2-methyl-1-phenylsulfonyl-2-butene (7a) or 4-hydroxy-2-methyl-1-phenylsulfonyl-2-butene (7b). Expeditious total syntheses of coenzyme Q-10 and vitamin K2(20) have been demonstrated from these valuable key compounds 4a and 4b.