Elsevier

Carbohydrate Research

Volume 299, Issue 3, 21 April 1997, Pages 151-158
Carbohydrate Research

Authentic standards for the reductive-cleavage method. The positional isomers of partially methylated and acetylated or benzoylated 1,5-anhydro-l-rhamnitol

https://doi.org/10.1016/S0008-6215(97)00008-6Get rights and content

Abstract

Described herein is an efficient method for the synthesis of the eight positional isomers of methylated and acetylated or benzoylated 1,5-anhydro-l-rhamnitol. The compounds are generated simultaneously from 1,5-anhydro-l-rhamnitol by sequential partial methylation and benzoylation. The individual isomers are obtained in pure form by high-performance liquid chromatography. Debenzoylation and acetylation yielded the desired 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. 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.

The title compounds were obtained in pure form from 1,5-anhydro-l-rhamnitol by sequential methylation, benzoylation, and fractionation by HPLC. Debenzoylation and acetylation yielded the corresponding acetates.

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