Authentic standards for the reductive-cleavage method. The positional isomers of partially methylated and acetylated or benzoylated 1,5-anhydro-D-fucitol.
Described herein is an efficient method for the synthesis of the eight positional isomers of methylated and acetylated or benzoylated 1,5-anhydro-D-fucitol. The compounds are generated simultaneously by partial methylation of 1,5-anhydro-D-fucitol and subsequent benzoylation, and the individual isomers are obtained in pure form by high-performance liquid chromatography. Debenzoylation of the latter and acetylation yielded the desired acetates. Reported herein are the 1H NMR spectra of the benzoates and the electron-ionization mass spectra of the acetates and the tri-O-methyl derivative. Also reported for the acetates and the tri-O-methyl derivative are their linear temperature programmed gas-liquid chromatography retention indices on three different capillary columns.
Elvebak
L E
LE
Department of Chemistry, University of Minnesota, Minneapolis 55455.
Schmitt
T
T
Gray
G R
GR
D000085:Acetates / Q000737:chemistry; D000107:Acetylation; D001565:Benzoates / Q000737:chemistry; D019817:Benzoic Acid; D002625:Chemistry, Organic / Q000592:standards*; D002851:Chromatography, High Pressure Liquid; D004376:Galactitol / Q000031:analogs & derivatives* / Q000737:chemistry; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008745:Methylation; D010084:Oxidation-Reduction
D000085:Acetates; D001565:Benzoates; D004376:Galactitol; D019817:Benzoic Acid