Synthesis and characterization of authentic standards for the reductive-cleavage method. The positional isomers of partially methylated and acetylated or benzoylated 1,4-anhydro-L-fucitol.
Described herein is the synthesis of all positional isomers of methylated and acetylated or benzoylated 1,4-anhydro-L-fucitol. The benzoates are generated simultaneously from 1,4-anhydro-L-fucitol by sequential partial methylation and benzoylation or sequential partial benzoylation and methylation. The individual isomers are obtained in pure form by high-performance liquid chromatography. Debenzoylation and acetylation provided the corresponding acetates. The 1H NMR spectra of the benzoates and the electron-ionization mass spectra of the acetates and the tri-O-methyl derivative are reported herein as are the linear temperature programmed gas-liquid chromatography retention indices of the acetates and the tri-O-methyl derivative on three different capillary columns.
Wang
N
N
Department of Chemistry, University of Minnesota, Minneapolis 55455, USA.
Elvebak
L E
LE
Gray
G R
GR
D000085:Acetates / Q000138:chemical synthesis / Q000737:chemistry; D000107:Acetylation; D001565:Benzoates / Q000138:chemical synthesis / Q000737:chemistry; D002849:Chromatography, Gas; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008745:Methylation; D015394:Molecular Structure; D010084:Oxidation-Reduction; D012015:Reference Standards; D013402:Sugar Alcohols / Q000138:chemical synthesis / Q000737:chemistry* / Q000592:standards
C096717:1,4-anhydrofucitol; D000085:Acetates; D001565:Benzoates; D013402:Sugar Alcohols