895518-38-4

Basic information

• Product Name: (2R)-α-Tocopherol (Mixture of Diastereomers)
• Synonyms: (2R)-α-Tocopherol (Mixture of Diastereomers);(2R)-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-3,4-dihydrochromen-6-ol;(2R)-α-Tocopherol
• CAS NO: 895518-38-4
• Molecular Formula: C₂₉H₅₀O₂
• Molecular Weight: 430.7061
• Mol File: 895518-38-4.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (2R)-α-Tocopherol (Mixture of Diastereomers)(CAS DataBase Reference)
• NIST Chemistry Reference: (2R)-α-Tocopherol (Mixture of Diastereomers)(895518-38-4)
• EPA Substance Registry System: (2R)-α-Tocopherol (Mixture of Diastereomers)(895518-38-4)

Safety Data

• Hazardous Substances Data: 895518-38-4(Hazardous Substances Data)

Usage

Uses

(2R)-α-Tocopherol is one of the 8 stereoisomers contained in the racemic mixture of synthetic α-Tocopherol, a vitamin E substitute.

Upstream product

• 114499-45-5 3,7-dimethyloctanyl-1-magnesium bromide 
• 13786-84-0 3,7,11-trimethyldodecanal 
• 6750-34-1 3,7,11-trimethyldodecyl alcohol 
• 106-28-5 Farnesol 
• 174681-06-2 (E)-5-(5-(benzyloxy)-2-hydroxy-3,4,6-trimethylphenyl)-3-methylpent-2-en-1-ol 
• 59-02-9 vitamin E 
• 1192216-90-2 (2R)-6-(tert-butyldimethylsilyloxy)-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)chroman 
• 79397-72-1 (-)-(S)-6-benzyloxy-2,5,7,8-tetramethylchroman-2-carboxylic acid methyl ester 
• 79397-68-5 rac-2,6,10-trimethylundecen-1-en-3-ol 
• 53101-49-8 (S)-6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid 
• 70897-17-5 (S)-(+)-3,4-dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxylic acid methyl ester 

Downstream Products

• 1406-70-8 (2R,4'RS,8'RS)-α-tocopheryl acetate 

Relevant articles and documents

Enantioselective Cleavage of Cyclobutanols Through Ir-Catalyzed C?C Bond Activation: Mechanistic and Synthetic Aspects

The Ir-catalyzed conversion of prochiral tert-cyclobutanols to β-methyl-substituted ketones proceeds under comparably mild conditions in toluene (45–110 °C) and is particularly suited for the enantioselective desymmetrization of β-oxy-substituted substrates to give products with a quaternary chirality center with up to 95 % ee using DTBM-SegPhos as a chiral ligand. Deuteration experiments and kinetic isotope effect measurements revealed major mechanistic differences to related RhI-catalyzed transformations. Supported by DFT calculations we propose the initial formation of an IrIII hydride intermediate, which then undergoes a β-C elimination (C?C bond activation) prior to reductive C?H elimination. The computational model also allows the prediction of the stereochemical outcome. The Ir-catalyzed cyclobutanol cleavage is broadly applicable but fails for substrates bearing strongly coordinating groups. The method is of particular value for the stereo-controlled synthesis of substituted chromanes related to the tocopherols and other natural products.

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.

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).