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

✍ Scribed by Larry E. Elvebak II; Tony Schmitt; Gary R. Gray

Publisher: Elsevier Science
Year: 1993
Tongue: English
Weight: 761 KB
Volume: 246
Category: Article
ISSN: 0008-6215
DOI: 10.1016/0008-6215(93)84019-3

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✦ Synopsis

Described herein is an efficient method for the synthesis of the eight positional isomers of methylated and acetylated or benzoylated 1,5-anhydro-o-fucitol. The compounds are generated simultaneously by partial methylation of 1,5-anhydro-o-fucitol 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. Reported herein are the 'H 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.

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