69400-39-1

Upstream product

• 69371-87-5 (S)-(-)-6-benzyloxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-ylmethanol 
• 82299-59-0 (1S,2S)-1-((S)-6-Benzyloxy-2,5,7,8-tetramethyl-chroman-2-yl)-propane-1,2-diol 
• 79397-72-1 (-)-(S)-6-benzyloxy-2,5,7,8-tetramethylchroman-2-carboxylic acid methyl ester 
• 700-13-0 Trimethylhydroquinone 
• 4537-09-1 1,4-dimethoxy-2,3,5-trimethyl-benzene 
• 69821-05-2 1-bromo-2,5-dimethoxy-3,4,6-trimethylbenzene 
• 100-39-0 benzyl bromide 
• 6153-06-6 (E)-3-methylpent-2-en-4-yn-1-ol 
• 357172-73-7 2-[(S)-3-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-3-hydroxy-butyl]-3,5,6-trimethyl-[1,4]benzoquinone 
• 357172-72-6 3-(2,5-Dimethoxy-3,4,6-trimethyl-phenyl)-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-propan-1-one 
• 357172-75-9 (S)-2-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,5,7,8-tetramethyl-chroman-6-ol 
• 196600-49-4 (R)-1-((S)-6-Hydroxy-2,5,7,8-tetramethyl-chroman-2-yl)-ethane-1,2-diol 
• 262849-34-3 (S)-(+)-2-acetoxymethyl-6-benzyloxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran 
• 163037-44-3 Acetic acid (S)-6-hydroxy-2,5,7,8-tetramethyl-chroman-2-ylmethyl ester 

Downstream Products

• 59-02-9 Tocopherol 
• 918876-09-2 (S)-6-(benzyloxy)-2-(12-(benzyloxy)dodec-1-enyl)-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromene 
• 895518-38-4 vitamin E 
• 1406-70-8 (2R,4'RS,8'RS)-α-tocopheryl acetate 
• 261929-80-0 C₃₄H₄₄O₂ 
• 1002090-21-2 (S,E)-ethyl-3-(6-benzyloxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromen-2-yl)acrylate 
• 221324-51-2 (S)-6-(benzyloxy)-3,4-dihydro-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxylic acid 
• 53101-49-8 (S)-6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid 
• 77171-98-3 vitamin E 

Relevant academic research and scientific papers

Stereoselective total synthesis method of (2R, 4 'R, 8' R)-alpha-tocopherol

The invention discloses a stereoselective total synthesis method of (2R, 4 'R, 8' R)-alpha-tocopherol. The method comprises the following steps: performing iodination on trimethylhydroquinone serving as a raw material to generate aromatic halide, and performing Heck reaction and Pd/C hydrogenation on the aromatic halide and diester containing a terminal olefinic bond to form saturated aromatic diester; then diester is selectively hydrolyzed to generate monoester with high optical activity, and a chiral three-dimensional center is constructed; then carrying out methylsulfonyl chlorination and lithium aluminum hydride reduction to form a methyl-containing chiral compound; carrying out oxidation ring closing and hydrogenation reduction to construct a chiral chroman mother nucleus; then carrying out benzyl protection and Wittig reaction, and realizing carbon-carbon bond connection with C15 * fat long-chain phosphine salt; finally, double bonds are reduced to obtain (2R, 4 'R, 8' R)-alpha-tocopherol I. The method has the advantages that the raw materials are easy to obtain, the reaction condition is mild, the operation is simple and convenient, the used lipase has good stability, the catalytic form is green and environment-friendly, and the industrial application value is realized.

Screening of a virtual mirror-image library of natural products

We established a facile access to an unexplored mirror-image library of chiral natural product derivatives using d-protein technology. In this process, two chemical syntheses of mirror-image substances including a target protein and hit compound(s) allow the lead discovery from a virtual mirror-image library without the synthesis of numerous mirror-image compounds.

Gold-catalyzed asymmetric allylic substitution of free alcohols: An enantioselective approach to chiral chromans with quaternary stereocenters for the synthesis of Vitamin E and analogues

The enantioselective synthesis of α- and γ-tocopherol (the most biologically active members of vitamin E family) and analogues has been accomplished employing a new enantioselective gold catalyzed intramolecular allylic alkylation reaction followed by an olefin cross-metathesis as key steps. The methodology proved to be applicable to different olefins highlighting its potential for the synthesis of diverse libraries. The enantioselective synthesis of α- and γ-tocopherol (the most biologically active members of vitamin E family) and analogues has been accomplished employing an enantioselective gold-catalyzed intramolecular allylic alkylation reaction followed by an olefin cross-metathesis as key steps (see scheme).

New possibilities in a synthesis of (2R,4'R,8'R)-α-tocopherol (natural vitamin E)

New methods for the synthesis of homochiral C14 and C 15-terpenoids desired as building blocks for phytilic side chain of natural α-tocopherol have been developed. A natural phytone resulted from the proposed effective method of chlo

Enantioselective transesterification of (±)-6-benzyloxy-2,5,7,8- tetramethyl-3,4-dihydro-2H-1-benzopyran-2-ylmethanol catalyzed by the Amano PS lipase in the ionic liquid [bmim]PF6

(S)-(-)-6-Benzyloxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2- ylmethanol, a synthon for the design of natural α-tocopherol, was obtained by kinetically selective acetylation of the corresponding racemic alcohol in the presence of the Amano PS lipase from Burkholderia cepacia in the ionic liquid 1-butyl-3-methylimidazolinium hexafluorophosphate ([bmim]PF6).

Reagent directing group controlled organic synthesis: Total synthesis of (R,R,R,)-α-tocopherol

(Chemical Equation Presented) The direct approach: The efficient use of substrate control has served as the basis for the enantioselective total synthesis of (R,R,R)-α-tocopherol. A single reagent directing group (ortho-diphenylphosphanyl benzoate, o-DPPB) served to control the stereoselectivity of a rhodium-catalyzed hydroformylation reaction and the directed allylic substitution as the fragment-coupling step (see picture).

Improved synthesis of tocopherol fatty alcohols and analogs: microglial activation modulators

The synthesis of tocopherol fatty alcohols (TFAs), potent microglial activation modulators, was achieved via C-alkylation of trimethylhydroquinone. Several analogs, in particular water-soluble prodrugs, have been synthesized using a Wittig reaction and th

Tocopherol, tocotrienol, other chromane, and their side chain deriv. and method for using the same

The present invention provides an antiproliferative compound having the structural formula wherein X is oxygen, nitrogen or sulfur; Y is selected from the group consisting of oxygen, nitrogen and sulfur wherein when Y is oxygen or nitrogen, n is 1 and when Y is sulfur, n is 0. Also provided is a method for inducing apoptosis in a cell comprising administering a composition comprising a compound having said structural formula.

Tocopherols, tocotrienols, other chroman and side chain derivatives and uses thereof

The present invention provides an antiproliferative compound having a structural formula where X and Y independently are oxygen, nitrogen o r sulfur; R1 is alkyl, alkenyl, alkynyl, aryl, heteroaryl, carboxylic acid, carboxylate, carboxamide, ester, thioamide, thiolacid, thiolester, saccharide, alkoxy-linked saccharide, amine, sulfonate, sulfate, phosphate, alcohol, ethers or nitriles; R2 and R3 are hydrogen or R4; R4 is methyl, benzyl carboxylic acid, benzyl carboxylate, benzyl carboxamide, benzylester, saccharide or amine; and R5 is alkenyl; where when Y is nitrogen, said nitrogen is substituted with R6, wherein R6 is hydrogen or methyl. Also provided are methods for treating a cell proliferative disease and for inducing apoptosis in a cell comprising administering this compound is also provided.

A new synthetic route to (S)-chroman aldehyde, a key chiral precursor of vitamin E

A highly stereocontrolled synthetic route to (S)-chroman aldehyde has been developed which starts with trimethyl-p-hydroquinone and (R)-glycerladehyde acetonide and employs as key steps the Michael addition of the aromatic copper species onto the (R)-4-acryloyl-1,3-dioxolane followed by the highly diastereoselective methylation of the resulting ketone adduct.