69400-39-1

Basic information

• Product Name: 2H-1-Benzopyran-2-carboxaldehyde, 3,4-dihydro-2,5,7,8-tetramethyl-6-(phenylmethoxy)-, (2S)-
• CAS NO: 69400-39-1
• Molecular Formula: C21H24O3
• Molecular Weight: 324.42
• Mol File: 69400-39-1.mol
• Article Data: 18

Chemical Properties

• CAS DataBase Reference: 2H-1-Benzopyran-2-carboxaldehyde, 3,4-dihydro-2,5,7,8-tetramethyl-6-(phenylmethoxy)-, (2S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2H-1-Benzopyran-2-carboxaldehyde, 3,4-dihydro-2,5,7,8-tetramethyl-6-(phenylmethoxy)-, (2S)-(69400-39-1)
• EPA Substance Registry System: 2H-1-Benzopyran-2-carboxaldehyde, 3,4-dihydro-2,5,7,8-tetramethyl-6-(phenylmethoxy)-, (2S)-(69400-39-1)

Safety Data

• Hazardous Substances Data: 69400-39-1(Hazardous Substances Data)

Upstream product

• 221324-50-1 benzyl (S)-6-(benzyloxy)-3,4-dihydro-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxylate 
• 53101-49-8 (S)-6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid 
• 171270-07-8 (6-Benzyloxy-3,4-dihydro-2,5,7,8-tetramethyl-2H-1-benzopyran-2-yl)methanol 
• 69821-05-2 1-bromo-2,5-dimethoxy-3,4,6-trimethylbenzene 
• 6153-06-6 (E)-3-methylpent-2-en-4-yn-1-ol 
• 69427-83-4 (S)-(+)-6-hydroxy-2,5,7,8-tetramethylchroman-2-methanol 
• 100-39-0 benzyl bromide 
• 174681-06-2 (E)-5-(5-(benzyloxy)-2-hydroxy-3,4,6-trimethylphenyl)-3-methylpent-2-en-1-ol 
• 100-44-7 benzyl chloride 
• 105857-79-2 C₂₇H₄₄O₄Si 
• 105857-82-7 2-{(1R,2S,5R)-1-[(R)-6-Benzyloxy-5,7,8-trimethyl-2-(tetrahydro-pyran-2-yloxymethyl)-chroman-2-ylmethoxy]-2-isopropyl-5-methyl-cyclohexyl}-1-phenyl-ethanone 
• 105881-91-2 2-[(1R,2S,5R)-1-((S)-6-Benzyloxy-2-hydroxymethyl-5,7,8-trimethyl-chroman-2-ylmethoxy)-2-isopropyl-5-methyl-cyclohexyl]-1-phenyl-ethanone 
• 105857-81-6 2-[(1R,2S,5R)-1-((S)-2-Hydroxymethyl-5,7,8-trimethyl-6-trimethylsilanyloxy-chroman-2-ylmethoxy)-2-isopropyl-5-methyl-cyclohexyl]-1-phenyl-ethanone 
• 105857-83-8 [(R)-6-Benzyloxy-5,7,8-trimethyl-2-(tetrahydro-pyran-2-yloxymethyl)-chroman-2-yl]-methanol 

Downstream Products

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

Relevant articles and documents

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.

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).

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).