82353-24-0

Upstream product

• 1838-94-4 isoprene epoxide 
• 34407-31-3 1-bromo-3,4-dimethoxy-2,5-bis(methoxymethoxy)-6-methylbenzene 
• 39068-88-7 2,3,4-trimethoxy-6-methylphenol 
• 3066-90-8 2,3-dimethoxy-5-methylbenzene-1,4-diol 
• 605-94-7 2,3-Dimethoxy-5-methyl-1,4-benzoquinone 
• 872979-65-2 ethyl (2E)-4-[3,4-dimethoxy-2,5-bis(methoxymethoxy)-6-methylphenyl]but-2-enoate 
• 872979-63-0 2-[3,4-dimethoxy-2,5-bis(methoxymethoxy)-6-methylphenyl]ethanol 
• 872979-64-1 2-[3,4-dimethoxy-2,5-bis(methoxymethoxy)-6-methylphenyl]ethanal 
• 67991-59-7 2,3-dimethoxy-1,4-bis(methoxymethoxy)-5-methylbenzene 
• 82343-04-2 (2E)-4-(3,4-dimethoxy-2,5-bis(methoxymethoxy)-6-methylphenyl)-2-methylbut-2-en-1-ol 

Downstream Products

• 82349-09-5 1-{(2E,6E,10E,14E,18E,22E,26E,30E,34E)-3,7,11,15,19,23,27,31,35,39-decamethyl-5-[(4-methylphenyl)sulfonyl]tetraconta-2,6,10,14,18,22,26,30,34,38-decaen-1-yl}-3,4-dimethoxy-2,5-bis(methoxymethoxy)-6-methylbenzene 
• 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 
• 303-98-0 ubidecarenone 

Relevant academic research and scientific papers

Synthetic studies on coenzyme Q10: Part 1 - An efficient and highly stereocontrolled synthesis of coenzyme Q10 via a C 5+C45 strategy

A practical, highly stereoselective ten-step synthesis of coenzyme Q 10 (1) has been accomplished (overall yield ca. 28%), starting from commercially available 2,3-dimethoxy-5-methylbenzoquinone (Scheme). The introduction of the first side-chain isoprenyl group with (E)-configuration (compound 6) was realized by means of a coupling reaction of the aromatic system 3 with oxirane, followed by Swern oxidation and Wittig olefination. The tosyl (Ts) group in the sulfone 9 was selectively removed with sodium naphthalenide in THF to afford 1.

An Efficient Stereoselective Synthesis of Co-enzyme Q10

Co-enzyme Q10 was efficiently synthesised by stereo- and regio-selective prenylation of the protected hydroquinone (2) with isoprene epoxide and solanesyl p-tolyl sulphone in a good overall yield.