186537-56-4

Upstream product

• 21980-71-2 neophytadiene 
• 700-13-0 Trimethylhydroquinone 
• 150-86-7 phytol 
• 395645-30-4 (3RS,7R,11R)-3,7,11,15-tetramethylhexadec-1-en-3-ol 
• 120680-10-6 6-Methoxymethoxy-2,5,7,8-tetramethyl-2-((4R,8R)-4,8,12-trimethyl-tridecyl)-2H-chromene 
• 16825-16-4 (6R,10R)-6,10,14-trimethylpentadecan-2-one 
• 4444-13-7 (Z)-1-bromo-3,7,11,15-tetramethylhexadec-2-ene 
• 1629168-06-4 C₂₉H₄₈O₄ 
• 105470-79-9 (3R,7R,5E)-3,7,11-trimethyldodecan-1-al 
• 1629168-03-1 1-(2-hydroxy-5-methoxy-3,4,6-trimethylphenyl)ethanone 
• 130422-86-5 4-methoxy-2,3,5-trimethylphenol 
• 1629281-17-9 C₁₅H₂₂O₃ 
• 6750-34-1 (3R,7R)-hexahydrofarnesol 
• 112109-69-0 4-hydroxy-2,3,5-trimethylphenyl pivalate 

Downstream Products

• 121707-15-1 (2RS,4'R,8'R)-O-(3,5-dinitro-phenylcarbamoyl)-α-tocopherol 
• 5934-22-5 (2RS,4'R,8'R)-O-(4-Nitro-phenylcarbamoyl)-α-tocopherol 
• 121656-51-7 (2RS,4'R,8'R)-O-(3,5-dinitro-benzoyl)-α-tocopherol 
• 758720-42-2 α?tocopherol quinone 
• 59-02-9 Tocopherol 
• 18920-63-3 vitamin E 

Relevant academic research and scientific papers

Total synthesis of (2RS)-α-tocopherol through Ni-catalyzed 1,4-addition to a chromenone intermediate

A novel strategy for the total synthesis of α-tocopherol ("vitamin E") was elaborated on the basis of the conjugate addition of AlMe3 (as a methyl anion equivalent) to a 2-substituted chromenone. Starting from trimethylhydroquinone and (R,R)-he

Oxalate as an activated ester group in lipase-catalyzed enantioselective hydrolysis: A versatile approach to d-α-tocopherol

The d-α-tocopherol was synthesized effectively by enzyme-catalyzed enantioselective hydrolysis of dl-α-tocopherol oxalate. The enzymes can recognize a stereogenic carbon atom remote from the reaction site.

Fast multigram scale microwave-assisted synthesis of Vitamin E and C10-, C15-analogues under vacuum

A novel protocol for the microwave-assisted synthesis of (all-rac)-α-tocopherol, including its C10- and C15-analogues, is reported. A rotating microwave reactor working under vacuum favoured the rapid evaporation of condensation water and solvent at the end of the process. The main advantages of this fast procedure are its good yield, selectivity, versatility, lower solvents and energy consumption, easier workup and-scalability.

Process of separating chiral isomers of chroman compounds and their derivatives and precursors

The present invention relates to a process of separating chiral isomers of chroman compounds, particularly tocopherols and tocotrienols as well as the esters and intermediates thereof. It has been found that this process allows a separation of the desired isomer with a higher yield and enables the use of the non-desired isomers in a very efficient way. Said process is particularly useful when implemented in an industrial process. Furthermore, it has been found that this process allows using isomer mixtures as they result from traditional industrial synthesis.

InIII-catalysed tandem C-C and C-O bond formation between phenols and allylic acetates

Indium triflate catalysed tandem allylation-intramolecular hydroalkoxylation was efficiently carried out by using 1 mol-% of the catalyst under mild conditions to afford the dihydrobenzopyran ring system (chroman-type structure) in good yields. Kinetic, mechanistic and theoretical studies are also presented. Tandem allylation-intramolecular hydroalkoxylation carried out in the presence of an indium catalyst (1 mol-%) under mild conditions provides the dihydrobenzopyranring system in good yields. Kinetic, mechanistic and theoretical studies are presented.

Total synthesis of naturally occurring α-tocopherol. Assymetric alkylation and asymmetric epoxidation as means to introduce (R)-configuration at C(2) of the chroman moiety

Based on the reductive, stereospecific ring closure of (2R,4'R,8'R)-α-'Tocopherylquinone' or corresponding analogues with a short, functionalized side chain (B, Scheme 1) to 1 resp. the chroman system of 1 (C), two different approaches for the introduction of the required tertiary methyl-substituted alcohol structure in the side chain of the aromatic precursors (A, Scheme 1) were developed. The first approach uses asymmetric alkylation in three different versions featuring a) diastereoselective steering with chiral auxiliaries I-IV (Scheme 2) attached as esters to α-keto acids, b) intermediate transfer of chirality in an ester enolate (from 18, Scheme 4) derived from an optically active α-hydroxyacid, c) enantioselective alkylation of phytenal (20) and subsequent ring closure with chirality transfer (Schemes 5-7). The second approach is based on the asymmetric epoxidation of β-metallylalcohol (Sharpless epoxidation), the corresponding epoxyalcohol being converted in situ to the (S)- or (R)-chlorodiol (S)- and (R)-29, respectively, for isolation (Schemes 8 and 9). Nucleophilic epoxide opening with a (3R,7R)-3,7,11-trimethyldodecyl (C15**) and an ArCH2 unit in appropriate sequence is used to assemble the C-framework of the target molecule via corresponding epoxide intermediates from either chlorodiol. Combined with the use of the methoxymethyl-ether function for protection of the hydroquinone system, the epoxide approach provides a short route to 1 (Scheme 10).