FLORENTINA DUICA, SILVIA STEFANIA GITMAN, DUMITRU PETRU IGA<br>\Synthesis of 1,2,5,6-tetra-O-acetyl-3-O-allyl <br>ab-D-galactofuranose, a Versatile Precursor of Pyranosylated and Furanosylated Glycoconjugates

FLORENTINA DUICA, SILVIA STEFANIA GITMAN, DUMITRU PETRU IGA
\Synthesis of 1,2,5,6-tetra-O-acetyl-3-O-allyl
ab-D-galactofuranose, a Versatile Precursor of Pyranosylated and Furanosylated Glycoconjugates

Abstract:

Dissolution of D-galactose in N,N-dimethylformamide and then acetonation by boiling with acetone and anhydrous copper sulfate, produced a mixture of 1,2-5,6-di-O-isopropylidene-a-D-galactofuranose and 1,2-3,4-di-O-isopropylidene-a-D-galactopyranose. The first isomer was separated by column chromatography on silica gel and allylated in N,N-dimethylformamide with allyl bromide in the presence of NaH. A smaller portion of di-isopropylidene furanose was acetylated and another one was left aside per se. Then the terminal isopropylidene group from all three compounds was selectively removed by stirring with dilute acetic acid. The newly formed hydroxy groups were peracetylated and then the other isopropylidene group was removed, and the reaction products peracetylated. All intermediates as well as the final products were characterized chemically and by 1H NMR spectroscopy. As an application, the allylated tetra-acetylated sugar was converted to 2,5,6-tri-O-acetyl-3-O-allyl ab-D-galactofuranosyl bromide and the latter product used for galactofuranosylation of cholesterol. Keywords: 1,2-5,6-Di-O-isopropylidene 3-O-allyl a-D-galactofuranose, 3-O-allyl-D-galactose, D-galactopyranose, NMR spectra

Issue: 2015, Volume 66, Issue 12

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