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GC-MS Characterization of Acetylated O-glucofuranosides: Direct Glucosylation of Volatile Alcohols from Unprotected Glucose

Croatian International Relations Review

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Title GC-MS Characterization of Acetylated O-glucofuranosides: Direct Glucosylation of Volatile Alcohols from Unprotected Glucose
GC-MS karakterizacija acetiliranih O-glukofuranozida: izravna glukozilacija isparljivih alkohola iz nezaštićene glukoze
 
Creator Jerković, Igor
Mastelić, Josip
Blažević, Ivica
Šindler-Kulyk, Marija
Vikić-Topić, Dražen
 
Subject direct glucosylation using FeCl3; glucofuranosides and glucopyranosides; GC-MS spectra of glucofuranoside tetraacetates
 
Description O-Glucosylation of 1-pentanol, 1-octanol, 2-phenylethanol, benzyl alcohol, (±)-2-pentanol and (±)-menthol in 1,4-dioxane, using anhydrous FeCl3, afforded anomeric mixture of the corresponding
glucofuranosides as major and glucopyranosides as minor products in overall yields 20–52 %. Practical advantages of GC-MS for characterizing the prepared acetylated glucofuranosides are in the focus of this paper. Glucofuranoside tetraacetate spectra contain characteristic signals of glucone (acetylated glucose) along with fragments of the aglucone moiety. The mass range was 50–600 mass units and acetyl ion was not present in the spectra, which is of interest
for differentiating glucofuranoside and glucopyranoside tetraacetates.
O-glukozilacija 1-pentanola, 1-oktanola, 2-feniletanola, benzil-alkohola, (±)-2-pentanola i (±)-mentola u 1,4-dioksanu, rabeći bezvodni FeCl3, dala je odgovarajuće glukofuranozide kao glavne i glukopiranozide kao sporedne produkte s ukupnim prinosima 20–52 %. Praktične prednosti GC-MS za karakterizaciju pripravljenih glukofuranozida su u žari{tu ovoga rada. Spektri glukofuranozid tetraacetata sadrže karakteristične signale glukona (acetilirane glukoze) zajedno s fragmentima aglukonskoga dijela. Interval praćenja masa bio je 50–600 masenih jedinica i acetil-ion nije bio prisutan u spektrima, {to je od interesa za razlikovanje glukofuranozid i glukopiranozid tetraacetata.
 
Publisher Croatian Chemical Society
 
Date 2005-06-15
 
Type text
info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
 
Format application/pdf
 
Identifier http://hrcak.srce.hr/27
http://hrcak.srce.hr/file/27
 
Source Croatica Chemica Acta
ISSN 0011-1643 (Print)
ISSN 1334-417X (Online)
Volume 78
Issue 2
 
Language eng
 
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