Absolute configuration ofcis‐5,6‐dihydrodiol enantiomers derived from helical conformers of 1,12‐dimethylbenz[a]anthracene
作者:
Shen K. Yang,
Mohammad Mushtaq,
Peter P. Fu,
期刊:
Chirality
(WILEY Available online 1990)
卷期:
Volume 2,
issue 1
页码: 58-64
ISSN:0899-0042
年代: 1990
DOI:10.1002/chir.530020109
出版商: Alan R. Liss, Inc.
关键词: 1,12‐dimethylbenz[α]anthracene;helical conformers;cis‐5,6‐dihydrodiol;high‐performance liquid chromatography;chiral stationary phase;optical isomers;resolution of enantiomers;absolute configuration;circular dichroism spectra
数据来源: WILEY
摘要:
Abstract1,12‐Dimethylbenz[α]anthracene (1,12‐DMBA)cis‐5,6‐dihydrodiol was synthesized by oxidation of 1,12‐DMBA with osmium tetroxide in pyridine in low yield (⩽3%) and was purified by sequential use of reversed‐phase and normal‐phase HPLC. Two pairs of 1,12‐DMBAcis‐5,6‐dihydrodiol enantiomers, derived from P (right‐handed helix) and M (left‐handed helix) conformers, were eluted as a single chromatographic peak on both reversed‐phase and normal‐phase HPLC. However, these four enantiomers were resolved by sequential use of two chiral stationary phase (CSP) HPLC columns. CSP (Pirkle type I) columns were packed with either (R)‐N‐(3,5‐dinitrobenzoyl)phenylglycine or (S)‐N‐(3,5‐dinitrobenzoyl)leucine, which is ionically bonded to γ‐aminopropylsilanized silica. Absolute configurations of enantiomers were determined by comparing their circular dichroism spectra with those of conformationally similarcis‐5,6‐dihydrodiol enantiomers of 4‐methylbenz[α]anthracene and 7,12‐dimethyl
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