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  • Title: Authentic standards for the reductive-cleavage method. The positional isomers of partially methylated and acetylated or benzoylated 1,5-anhydro-D-mannitol.
    Author: Elvebak LE, Cha HJ, McNally P, Gray GR.
    Journal: Carbohydr Res; 1995 Sep 08; 274():71-83. PubMed ID: 7585714.
    Abstract:
    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.
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