359643-67-7

Upstream product

• 359010-66-5 4-bromo-3-methyl-2-butenyl sulfide 
• 359010-62-1 1,5-di(phenylsulfonyl)-3,7,11-trimethyl-2,6,10-dodecatriene 
• 359010-60-9 5-phenylsulfonyl-1-phenylthio-3,7,11-trimethyl-2,6,10-dodecatriene 
• 1838-94-4 isoprene epoxide 
• 108-98-5 thiophenol 
• 57282-70-9 (E)-4-hydroxy-3-methyl-2-butenyl phenyl sulfide 
• 56691-80-6 geranyl phenyl sulfone 
• 359010-59-6 4-bromo-3-methyl-2-butenyl phenyl sulfide 

Downstream Products

• 359643-76-8 7,7',11,11'-tetra(phenylsulfonyl)-7,7',8,8',11,11',12,12'-octahydrolycopene 
• 502-65-8 lycopene 
• 359643-74-6 Di(5,9-di(phenylsulfonyl)-3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraenyl) sulfone 

Relevant academic research and scientific papers

Process for preparing carotenoid polyene chain compounds and intermediates for preparing the same

The present invention provides an intermediate compound used for synthesis of polyene chain structure, that is an important moiety of carotenoid compounds, a process for preparing the same, and carotenoid polyene chain compounds prepared by using the intermediate, and, in particular, a process for preparing lycopene. The process for preparing the carotenoid polyene chain compound employs an allylic sulfone compound as starting material, which is reacted with C-5 sulfide compound to extend the carbon chain. The resultant thio-sulfone compound is oxidized, and the obtained disulfone compound is combined with C-10 di(haloallylic) sulfide compound to form a chain compound containing the desired number of carbon atoms. Then, the diallylic sulfone obtained by oxidation of the diallylic sulfide is subjected to Ramberg-Baklund reaction in order to form the central triene bond. After removal of sulfonyl groups, carotenoid polyene chain compound is obtained.

A highly efficient chain-extension process in the systematic syntheses of carotenoid natural products

Successive elongation by a C5 unit is possible when an allylic sulfone is couple with 4-bromo-3-methyl-2-butenyl phenyl sulfide (1). The thiosulfone compound formed was then oxidized to the corresponding disulfone, which, upon coupling with another equivalent of 1 and oxidation, produced the trisulfone 2, again elongated by a C5 unit (see scheme). This process, which can be repeated again, is the basis for a highly efficiently synthesis of carotenoids.