ISSN:
0170-2041
Keywords:
Thiophen-3-ol, tetrahydro-2-methyl-
;
Flavor substances, chiral
;
Chirality and odor
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Description / Table of Contents:
Stereoisomeric Flavor Substances XXXI1). - Tetrahydro-2-methylthiophen-3-ol - Structure and Properties of the StereoisomersTetrahydro-2-methylthiophen-3-ol (6) has been synthesized and separated by liquid chromatography to yield cis (6a/6a′) and trans isomers (6b/6b′). Using (S)-tetrahydro-5-oxo-2-furancarboxylic acid chloride, 6a/6a′ and 6b/6b′ are transformed into the diastereomeric esters 7-10 which are separated by liquid chromatography. Hydrolysis of the esters yields the optically pure stereoisomers 6a, 6a′, 6b, and 6b′. Absolute configuration and sensory characteristics of these stereoisomers are given.
Notes:
Tetrahydro-2-methylthiophen-3-ol (6) wurde synthetisiert und flüssigkeitschromatographisch in cis- (6a/6a′) und trans-Isomere (6b/6b′) getrennt. Durch Umsetzung mit (S)-Tetrahydro-5-oxo-2-furancarbonsäurechlorid werden aus 6a/6a′ und 6b/6b′ die diastereomeren Ester 7-10 gebildet, deren flüssigkeitschromatographische Trennung und anschließende Hydrolyse zu den optisch reinen Stereoisomeren 6a, 6a′, 6b und 6b′ führt. Absolute Konfiguration und sensorische Bewertung der Stereoisomeren werden mitgeteilt.
Additional Material:
3 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.198919890237
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