Authentic standards for the reductive-cleavage method. The positional isomers of partially methylated and acetylated or benzoylated 1,5-anhydro-D-mannitol.
Described herein is an efficient method for the synthesis of the sixteen positional isomers of methylated and acetylated or benzoylated 1,5-anhydro-D-mannitol. The compounds are generated simultaneously by partial methylation of 1,5-anhydro-D-mannitol 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. The the benzoates and the electron-ionization mass spectra of the acetates and the tetra-O-methyl derivative are reported herein as are the linear temperature-programmed gas-liquid chromatography retention indices of the acetates and the tetra-O-methyl derivative on three different capillary columns.
Elvebak
L E
LE
Department of Chemistry, University of Minnesota, Minneapolis 55455, USA.
Cha
H J
HJ
McNally
P
P
Gray
G R
GR
D000085:Acetates / Q000138:chemical synthesis; D000107:Acetylation; D001565:Benzoates / Q000138:chemical synthesis; D002236:Carbohydrate Conformation; D002849:Chromatography, Gas; D002851:Chromatography, High Pressure Liquid; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy; D008353:Mannitol / Q000031:analogs & derivatives* / Q000737:chemistry / Q000592:standards; D008745:Methylation; D015394:Molecular Structure; D010084:Oxidation-Reduction; D012015:Reference Standards
D000085:Acetates; D001565:Benzoates; D008353:Mannitol; C042618:1,5-anhydro-mannitol