Synthesis and characterization of authentic standards for the analysis of ribofuranose-containing carbohydrates by the reductive-cleavage method.
Described herein is the synthesis of  all positional isomers of partially methylated and acetylated or benzoylated 1,4-anhydro-D-ribitol. The benzoates are generated simultaneously from 1,4-anhydro-D-ribitol 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. 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 and also for the acetates and the tri-O-methyl derivative, their linear temperature programmed gas-liquid chromatography retention indices on three different capillary columns.
Rozanas
C R
CR
Department of Chemistry, University of Minnesota, Minneapolis 55455, USA.
Wang
N
N
Vidlock
K
K
Gray
G R
GR
D000085:Acetates / Q000138:chemical synthesis / Q000737:chemistry; D000107:Acetylation; D001565:Benzoates / Q000138:chemical synthesis / Q000737:chemistry; D002241:Carbohydrates / Q000737:chemistry*; D002849:Chromatography, Gas; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008745:Methylation; D015394:Molecular Structure; D010084:Oxidation-Reduction; D012015:Reference Standards; D012255:Ribitol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000592:standards; D012266:Ribose / Q000032:analysis*
D000085:Acetates; D001565:Benzoates; D002241:Carbohydrates; C096718:1,4-anhydroribitol; D012255:Ribitol; D012266:Ribose