Separation of stereoisomers of several furan derivatives by capillary gas chromatography-mass spectrometry, supercritical fluid chromatography, and liquid chromatography using chiral stationary phases.
The direct separation of several stereoisomers (enantiomers and geometrical isomers) of furan derivatives, important intermediates for the synthesis of physiologically active natural products, was achieved using capillary gas chromatography/mass spectrometry with a per-O-methyl-beta-cyclodextrin, supercritical fluid chromatography and high-performance liquid chromatography with a tris(3,5-dimethylphenylcarbamate) of cellulose or amylose for the chiral stational phases, respectively. The temperature dependence of the peak resolution (Rs) and the retention factor (k) over the range of 110-130 degrees was studied using crotyl furfuryl ether in gas chromatography. Successive increases in the Rs value and of the difference between the k value of the E-isomer and the k value of the Z-isomer were observed when the gradient temperature was decreased. The per-O-methyl-beta-cyclodextrin column was suitable for use with volatile furan ethers whose molecular masses are between 150 and 180. In conclusion, the separation of thermally unstable furan derivatives was accomplished using supercritical fluid chromatography and high-performance liquid chromatography.
Kasai
Hiroko F
HF
Faculty of Pharmaceutical Sciences, Hoshi University, Ebara 2-4-41, Shinagawa-Ku, Tokyo 142-8501, Japan. kasai@hoshi.ac.jp
Tsubuki
Masayoshi
M
Takahashi
Kazunori
K
Shirao
Mika
M
Matsumoto
Yohichiro
Y
Honda
Toshio
T
Seyama
Yoshiyuki
Y
D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D025924:Chromatography, Supercritical Fluid / Q000379:methods*; D005663:Furans / Q000737:chemistry / Q000302:isolation & purification*; D008401:Gas Chromatography-Mass Spectrometry / Q000379:methods*; D009682:Magnetic Resonance Spectroscopy; D013237:Stereoisomerism; D013696:Temperature
D005663:Furans