Authentic standards for the reductive-cleavage method. The positional isomers of partially methylated and acetylated or benzoylated methyl 2-(acetylmethylamino)-2-deoxy-beta-D-glucopyranoside.
Described herein is the synthesis of eight positional isomers of methylated and acetylated or benzoylated methyl 2-(acetylmethylamino)-2-deoxy-beta-D-glucopyranoside. The compounds were generated simultaneously from methyl 2-(acetylmethylamino)-2-deoxy-beta-D-glucopyranoside by sequential partial methylation and benzoylation and isolated in pure form by high-performance liquid chromatography (HPLC). 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 (GLC) retention indices on three different capillary columns.
Elvebak
L E
LE
Primedica, Worcester, MA 01608, USA.
Smith
S O
SO
Gray
G R
GR
D000085:Acetates / Q000737:chemistry*; D000107:Acetylation; D000117:Acetylglucosamine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D001565:Benzoates / Q000737:chemistry; D002849:Chromatography, Gas; D002851:Chromatography, High Pressure Liquid; D005960:Glucosides / Q000138:chemical synthesis* / Q000737:chemistry; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry / Q000379:methods; D008745:Methylation; D015394:Molecular Structure; D012015:Reference Standards
D000085:Acetates; D001565:Benzoates; D005960:Glucosides; D000117:Acetylglucosamine