82343-04-2

Upstream product

• 1838-94-4 isoprene epoxide 
• 872979-65-2 ethyl (2E)-4-[3,4-dimethoxy-2,5-bis(methoxymethoxy)-6-methylphenyl]but-2-enoate 
• 944936-27-0 (tert-butyl){[(2E)-4-(3,4-dimethoxy-2,5-bis(methoxymethoxy)-6-methylphenyl)-2-methylbut-2-enyl]oxy}dimethylsilane 
• 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 
• 872979-63-0 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 
• 524960-39-2 {[(2E)-4-bromo-2-methyl-2-butenyl]oxy}(tert-butyl)dimethylsilane 
• 34407-31-3 1-bromo-3,4-dimethoxy-2,5-bis(methoxymethoxy)-6-methylbenzene 

Downstream Products

• 109952-74-1 Methanesulfonic acid (E)-4-(3,4-dimethoxy-2,5-bis-methoxymethoxy-6-methyl-phenyl)-2-methyl-but-2-enyl ester 
• 944936-28-1 1-[(2E)-4-chloro-3-methylbut-2-enyl]-3,4-dimethoxy-2,5-bis(methoxymethoxy)-6-methylbenzene 
• 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 
• 110012-76-5 co-enzyme Q₁₀ 
• 59242-49-8 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)-3,4-dimethoxy-2,5-bis-methoxymethoxy-6-methyl-benzene 
• 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 
• 944936-30-5 1-[(2E,6E,10E,14E,18E,22E,26E,30E,34E)-5-(4-chlorophenylsulfonyl)-3,7,11,15,19,23,27,31,35,39-decamethyltetraconta-2,6,10,14,18,22,26,30,34,38-decaenyl]-3,4-dimethoxy-2,5-bis(methoxymethoxy)-6-methylbenzene 
• 82353-24-0 1-[(2E)-4-bromobut-2-en-1-yl]-3,4-dimethoxy-2,5-bis(methoxymethoxy)-6-methylbenzene 

Relevant academic research and scientific papers

Synthetic studies on coenzyme Q10: Part 31) - An improved C5 + C45 approach to the stereoselective synthesis of coenzyme Q10 via metal-halogen exchange strategy

An efficient and stereoselective approach to the synthesis of coenzyme Q10 is described (Scheme). The MeOCH2-protected p-hydroquinone 4 containing the C5 (E)-allyl (tert-butyl) dimethylsilyl ether moiety was obtained via a halogen-lithium exchange of the MeOCH2-proctected 2-bromo-5,6-dimethoxy-3-methylhydroquinone 2 and subsequent addition to (E)-(tBuMe2Si)-OCH 2C(Me)= CHCH2Br (3). The reductive desulfonylation of compound 8, obtained from 4 via 5-7, was successfully carried out by employing Li/EtNH2.

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.