3-巯基-2-甲基戊醇的对映选择性合成及感官特性

Enantioselective syntheses and sensory properties of the 3-mercapto-2-methylpentanols.

作者信息

Sabater Lüntzel C, Widder S, Vössing T, Pickenhagen W

机构信息

Corporate Research, DRAGOCO Gerberding & Company, AG D-37601, Holzminden, Germany.

出版信息

J Agric Food Chem. 2000 Feb;48(2):424-7. doi: 10.1021/jf9908300.

DOI:10.1021/jf9908300

PMID:10691651

Abstract

3-Mercapto-2-methylpentanol, a new powerful flavor compound, exhibits two stereocenters giving rise to two pairs of diastereomers. To determine differences in the sensory properties, all four diastereomers and enantiomers were stereo- and enantioselectively synthesized. A highly diastereoselective aldol reaction using a chiral auxiliary was one of the key steps in the synthesis. Further derivatization yielded the enantiopure compounds. Odor thresholds in air and water were determined.

摘要

3-巯基-2-甲基戊醇是一种新型强效风味化合物，具有两个立体中心，可产生两对非对映异构体。为了确定感官特性的差异，对所有四种非对映异构体和对映体进行了立体选择性和对映选择性合成。使用手性助剂进行的高度非对映选择性羟醛缩合反应是合成中的关键步骤之一。进一步衍生化得到对映体纯的化合物。测定了其在空气和水中的气味阈值。