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Abstract
The regioselective C-2-O-acrylation and metacrylation of methyl 4,6-O-benzylidene-α-D-glucopyranoside and methyl 4,6-O-benzylidene-α-D-galactopyranoside through their corresponding organotin intermediates have been studied. Regioselectivity was achived through the formation of a tin chelate of the 2,3-diols. Thus, methyl 4,6-O-benzylidene-α-D-glucopyranoside and methyl 4,6-O-benzylidene-α-D-galactopyranoside were reacted with dibutylstannylene to give the corresponding dibutylstannylene acetal intermediates that were then reacted in a regioselective manner with acryloyl chloride or metacryloyl chloride in the presence of triethylamine (TEA) or pyridine to give the vinylic type monomeric compounds. The monomeric products containing glucose and galactose units from each reaction were separated by column chromatography using a gradient of n-hexane and ethyl acetate as eluant. The structure of the obtained compounds were confirmed using 1H-, 13C- and 2D NMR spectroscopy.
Highlights
Carbohydrates are naturally occuring bioorganic compounds which are found in biological systems [1]
We show that the methyl 4,6-O-benzylidene-2-O-acryloyl-α-D-gluco- and galactopyranoside and methyl 4,6-Obenzylidene-2-O-metacryloyl-α-D-gluco- and galactopyranosides are the major products in the reaction of acryloyl chloride and metacryloyl chloride with stannylene acetal intermediates derived from the examined carbohydrate molecules [21]
Scheme 2: Synthesis of acrylic monomers through dibutylstannylene acetal intermediates derived from methyl 4,6-O-benzylidene-α-D-glucopyranoside
Summary
Carbohydrates are naturally occuring bioorganic compounds which are found in biological systems [1]. Reactions of dibutylstannylene acetals of methyl 4,6-Obenzylidene-α-D-glucopyranoside and methyl 4,6-O-benzylidene-α-D-galactopyranoside with acryloyl chloride and metacryloyl chloride in the presence of TEA or pyridine were usually complete in 1h at room temperature and gave the monomers methyl 2-O, 3-O and 2,3-O-4,6-O-benzylidene-diacryloylα-D-glucopyranoside and or galactopyranoside, respectively, with high regioselectivity and in excellent yield [18,19]. We show that the methyl 4,6-O-benzylidene-2-O-acryloyl-α-D-gluco- and galactopyranoside and methyl 4,6-Obenzylidene-2-O-metacryloyl-α-D-gluco- and galactopyranosides are the major products in the reaction of acryloyl chloride and metacryloyl chloride with stannylene acetal intermediates derived from the examined carbohydrate molecules [21].
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