Total Synthesis of All Eight Stereoisomers of ?-Tocopheryl Acetate. Determination of their diastereoisomeric and enantiomeric purity by gas chromatography

Autor:	Clifford G. Scott, Giuseppe F. Weber, Gabriel Saucy, Noal Cohen, Rocco J. Lopresti, Christian Neukom
Rok vydání:	1981
Předmět:	Chromatography Chemistry Organic Chemistry Diastereomer Total synthesis Biochemistry Catalysis Inorganic Chemistry chemistry.chemical_compound Homogeneous Drug Discovery Organic chemistry Tocopheryl acetate Gas chromatography Physical and Theoretical Chemistry Enantiomer
Zdroj:	Helvetica Chimica Acta. 64:1158-1173
ISSN:	1522-2675 0018-019X
DOI:	10.1002/hlca.19810640422
Popis:	All eight stereoisomers of α-tocopheryl acetate have been synthesized in a state of high chemical and stereoisomeric purity. Key chiral side-chain intermediates were prepared from (+)-(S)-3-hydroxy-2-methylpropanoic acid. New routes to (2R, 4′ RS, 8′ RS)-α-tocopheryl acetate, a mixture of four diastereoisomers, were also developed. A sensitive gas chromatographic method was developed to determine the diastereoisomeric and enantiomeric purity of α-tocopherol samples as the methyl ethers. It was established for the first time that naturally occurring α-tocopherol is essentially a single enantiomer (2 R, 4′ R, 8′ R), synthetic all-rac-α-tocopherol an equimolar mixture of four racemates, and that natural (E)-(7 R, 11 R)-phytol is diastereoisomerically and enantiomerically homogeneous.
Databáze:	OpenAIRE
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