GC-MS characterization of acetylated O-glucofuranosides: direct glucosylation of volatile alcohols from unprotected glucose

Jerković, Igor; Mastelić, Josip; Blažević, Ivica; Sindler-Kulyk, Marija; Vikić-Topić, Dražen (2005) GC-MS characterization of acetylated O-glucofuranosides: direct glucosylation of volatile alcohols from unprotected glucose. Croatica Chemica Acta, 78 (2). pp. 313-318. ISSN 0011-1643

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Abstract

O-Glucosylation of 1-pentanol, 1-octanol, 2-phenylethanol, benzyl alcohol, (+/-)-2-pentanol and (+/-)-menthol in 1,4-dioxane, using anhydrous FeCl(3), 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 tetruacetate 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.

Item Type:	Article
Uncontrolled Keywords:	direct glucosylation using FeCl(3); glucofuranosides and glucopyranosides; GC-MS spectra of glucofuranoside tetraacetates; beta-D-glucopyranosides; glycosyl donors; d-galactose
Subjects:	NATURAL SCIENCES > Chemistry
Divisions:	NMR Center
Projects:	Project title Project leader Project code Project type Eterična ulja - glikozidi isparljivih spojeva - sinteza glikozida Josip Mastelić 0011010 MZOS Sintetska, fotokemijska i strukturna istraživanja heterocikličkih spojeva Marija Šindler 0125004 MZOS Nuklearna magnetska rezonancija i proračuni bioorganskih molekula Dražen Vikić-Topić 0098059 MZOS
Depositing User:	Dražen Vikić-Topić
Date Deposited:	06 Nov 2013 12:24
URI:	http://fulir.irb.hr/id/eprint/901

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