69371-87-5

Basic information

• Product Name: (S)-(-)-6-benzyloxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-ylmethanol
• Synonyms: (S)-(-)-6-benzyloxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-ylmethanol
• CAS NO: 69371-87-5
• Molecular Weight: 326.436
• Mol File: 69371-87-5.mol
• Article Data: 14

Chemical Properties

• CAS DataBase Reference: (S)-(-)-6-benzyloxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-ylmethanol(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(-)-6-benzyloxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-ylmethanol(69371-87-5)
• EPA Substance Registry System: (S)-(-)-6-benzyloxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-ylmethanol(69371-87-5)

Safety Data

• Hazardous Substances Data: 69371-87-5(Hazardous Substances Data)

Upstream product

• 69427-83-4 (S)-(+)-6-hydroxy-2,5,7,8-tetramethylchroman-2-methanol 
• 100-39-0 benzyl bromide 
• 584-08-7 potassium carbonate 
• 100-44-7 benzyl chloride 
• 865444-18-4 4-(benzyloxy)-2,3,5-trimethyl-6-(3-methylbut-3-en-1-yl)phenol 
• 105857-83-8 [(R)-6-Benzyloxy-5,7,8-trimethyl-2-(tetrahydro-pyran-2-yloxymethyl)-chroman-2-yl]-methanol 
• 163037-44-3 Acetic acid (S)-6-hydroxy-2,5,7,8-tetramethyl-chroman-2-ylmethyl ester 
• 171270-07-8 (6-Benzyloxy-3,4-dihydro-2,5,7,8-tetramethyl-2H-1-benzopyran-2-yl)methanol 
• 210174-90-6 methyl-6-(benzyloxy)-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromene-2-carboxylate 
• 86646-83-5 methyl 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylate 
• 56305-04-5 trolox 
• 479353-37-2 Acetic acid (S)-6-hydroxy-2-hydroxymethyl-5,7,8-trimethyl-chroman-2-ylmethyl ester 
• 105857-77-0 2,2-Bis-hydroxymethyl-5,7,8-trimethyl-chroman-6-ol 
• 906079-26-3 toluene-4-sulfonic acid 6-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-5,7,8-trimethyl-chroman-2-ylmethyl ester 

Downstream Products

• 906079-31-0 (R)-6-(benzyloxy)-2,5,7,8-tetramethyl-2-((3E,7E)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl)chromane 
• 906079-30-9 (2S)-6-(benzyloxy)-2,5,7,8-tetramethyl-2-((3E,7E)-4,8,12-trimethyl-2-(phenylsulfonyl)trideca-3,7,11-trien-1-yl)chromane 
• 1721-51-3 alpha-tocotrienol 
• 1263473-57-9 (S)-6-benzyloxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-ylmethyl (R)-α-methoxy-α-phenyl-α-trifluoromethylacetate 
• 1416422-45-1 (2S)-6-benzyloxy-2-methyl-2-(3,7,11-trimethyldodecyloxy-methyl)chroman 
• 78656-12-9 (2R,4’R,8’S)-α-tocopherol 
• 78656-13-0 (2R,4’S,8’R)-α-tocopherol 
• 59-02-9 Tocopherol 
• 77171-98-3 vitamin E 
• 906079-28-5 (S)-[3,4-dihydro-6-benzyloxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-yl]methyl trifluoromethane-sulfonate 
• 69400-39-1 (+) (S)-6-benzyloxy-2,5,7,8-tetramethyl-chroman-2-carbaldhyde 

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.

Enantioselective Halo-oxy- and Halo-azacyclizations Induced by Chiral Amidophosphate Catalysts and Halo-Lewis Acids

Catalytic enantioselective halocyclization of 2-alkenylphenols and enamides have been achieved through the use of chiral amidophosphate catalysts and halo-Lewis acids. Density functional theory calculations suggested that the Lewis basicity of the catalyst played an important role in the reactivity and enantioselectivity. The resulting chiral halogenated chromans can be transformed to α-Tocopherol, α-Tocotrienol, Daedalin A and Englitazone in short steps. Furthermore, a halogenated product with an unsaturated side chain may provide polycyclic adducts under radical cyclization conditions.

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.