64634-91-9Relevant academic research and scientific papers
Synthesis of coenzyme Q10
Oh, Eun-Taek,Taek Oh, Jung,Koo, Sangho,Jin Kim, Hee,Su, Liang,Yun, Inkyun,Nam, Kyunggu,Min, Jae-Hong,Woo Kim, Joon
, p. 4954 - 4962,9 (2020/08/24)
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
Synthetic studies on coenzyme Q10: Part 31) - An improved C5 + C45 approach to the stereoselective synthesis of coenzyme Q10 via metal-halogen exchange strategy
Yu, Xiong-Jie,Dai, Hui-Fang,Chen, Fen-Er
, p. 967 - 971 (2008/02/04)
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
Yu, Xiong-Jie,Chen, Fen-Er,Dai, Hui-Fang,Chen, Xu-Xiang,Kuang, Yun-Yan,Xie, Bin
, p. 2575 - 2581 (2007/10/03)
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.
Palladium-Catalyzed Regio- and Stereoselective Reduction of Allylic Compounds with LiHBEt3. Application to the Synthesis of Co-enzyme Q10
Mohri, Mitsunobu,Kinoshita, Hideki,Inomata, Katsuhiko,Kotake, Hiroshi,Takagaki, Hidetsugu,Yamazaki, Keiji
, p. 1177 - 1180 (2007/10/02)
Regio- and stereoselective desulfonylation of allylic sulfones with LiHBEt3 in the presence of a catalytic amount of was succesfully applied to the synthesis of co-enzyme Q10.It was found that this reduction system was applicable to a wide variety of allylic functional groups.
An Efficient Stereoselective Synthesis of Co-enzyme Q10
Sato, Kikumasa,Miyamoto, Osamu,Inoue, Seiichi,Yamamoto, Tomoya,Hirasawa, Yukihiko
, p. 153 - 154 (2007/10/02)
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.
