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Synthesis and characterization of authentic standards for the reductive-cleavage method. The positional isomers of partially methylated and acetylated or benzoylated 1,4-anhydro-l-fucitol

✍ Scribed by Nan Wang; Larry E. Elvebak II; Gary R. Gray

Publisher: Elsevier Science
Year: 1995
Tongue: English
Weight: 563 KB
Volume: 274
Category: Article
ISSN: 0008-6215
DOI: 10.1016/0008-6215(95)00081-4

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✦ Synopsis

Described herein is the synthesis of all positional isomers of methylated and acetylated or benzoylated 1,4-anhydro-L-fucitol. The benzoates are generated simultaneously from 1,4-anhydro-L-fucitol by sequential partial methylation and benzoylation or sequential partial benzoylation and methylation. The individual isomers are obtained in pure form by high-performance liquid chromatography. Debenzoylation and acetylation provided the corresponding acetates. The 1H NMR spectra of the benzoates and the electron-ionization mass spectra of the acetates and the tri-O-methyl derivative are reported herein as are the linear temperature programmed gas-liquid chromatography retention indices of the acetates and the tri-O-methyl derivative on three different capillary columns.

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