Authentic standards for the reductive-cleavage method. The positional isomers of partially methylated and acetylated or benzoylated 1,5-anhydro-D-glucitol.
Described is an efficient method for the synthesis of the sixteen positional isomers of methylated and acetylated or benzoylated 1,5-anhydro-D-glucitol. The compounds are generated simultaneously by partial methylation of 1,5-anhydro-D-glucitol 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 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, USA.
Gray
G R
GR
D000085:Acetates / Q000138:chemical synthesis; D000107:Acetylation; D001565:Benzoates / Q000138:chemical synthesis; D002236:Carbohydrate Conformation; D002849:Chromatography, Gas; D003847:Deoxyglucose / Q000737:chemistry* / Q000592:standards; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008745:Methylation; D015394:Molecular Structure; D010084:Oxidation-Reduction; D012015:Reference Standards; D013012:Sorbitol / Q000031:analogs & derivatives* / Q000737:chemistry* / Q000592:standards
D000085:Acetates; D001565:Benzoates; D013012:Sorbitol; C006584:1,5-anhydroglucitol; D003847:Deoxyglucose