Authentic standards for the reductive-cleavage method. The positional isomers of partially methylated and acetylated or benzoylated 1,5-anhydro-D-galactitol.
Described herein is an efficient method for the synthesis of the sixteen positional isomers of methylated and acetylated or benzoylated 1,5-anhydro-D-galactitol. The compounds are generated simultaneously by partial methylation of 1,5-anhydro-D-galactitol and subsequent benzoylation, and the individual isomers are obtained in pure form by high-performance liquid chromatography. Debenzoylation 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 tetra-O-methyl derivative. Also reported for the acetates and the tetra-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.
Abbott
C
C
Wall
S
S
Gray
G R
GR
D000107:Acetylation; D002849:Chromatography, Gas; D002851:Chromatography, High Pressure Liquid; D004376:Galactitol / Q000138:chemical synthesis* / Q000737:chemistry; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008745:Methylation
D004376:Galactitol