Authentic standards for the reductive-cleavage method: the positional isomers of partially methylated and acetylated or benzoylated 1,5-anhydro-L-arabinitol.
Described herein is the synthesis of the eight positional isomers of methylated and acetylated or benzoylated 1,5-anhydro-L-arabinitol. The compounds were generated simultaneously from 1,5-anhydro-L-arabinitol by sequential partial methylation and benzoylation and isolated in pure from by high-performance liquid chromatography. The desired acetates were obtained by debenzoylation and acetylation of the pure isomers. 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
Hercules, Inc., Research Center, Wilmington, DE 19808, USA.
McNally
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P
Gray
G R
GR
D000107:Acetylation; D001565:Benzoates / Q000032:analysis; D002236:Carbohydrate Conformation; D002849:Chromatography, Gas; D002853:Chromatography, Liquid; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008745:Methylation; D012015:Reference Standards; D013402:Sugar Alcohols / Q000737:chemistry* / Q000302:isolation & purification
C119043:1,5-anhydroarabinitol; D001565:Benzoates; D013402:Sugar Alcohols