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Molecules 2005, 10(7), 772-782; doi:10.3390/10070772

Regioselective Synthesis of Vinylic Derivatives of Common Monosccarides Through Their Activated Stannylene Acetal Intermediates

1
Lab of Dendrimers and Biopolymers, Faculty of Chemistry, University of Tabriz, Iran
2
Research Institute for Fundamental Sciences, Tabriz, Iran
*
Author to whom correspondence should be addressed.
Received: 16 April 2004 / Revised: 4 November 2004 / Accepted: 6 November 2004 / Published: 31 August 2005
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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-galactopyranosidethrough their corresponding organotin intermediates have been studied. Regioselectivitywas 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-galactopyranosidewere reacted with dibutylstannylene to give the corresponding dibutylstannylene acetalintermediates that were then reacted in a regioselective manner with acryloyl chloride ormetacryloyl chloride in the presence of triethylamine (TEA) or pyridine to give thevinylic type monomeric compounds. The monomeric products containing glucose andgalactose units from each reaction were separated by column chromatography using agradient of n-hexane and ethyl acetate as eluant. The structure of the obtained compoundswere confirmed using 1H-, 13C- and 2D NMR spectroscopy.
Keywords: Regioselectivity; monosaccharides; tin intermediates; acrylation and metacrylation Regioselectivity; monosaccharides; tin intermediates; acrylation and metacrylation
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Namazi, H.; Sharifzadeh, R. Regioselective Synthesis of Vinylic Derivatives of Common Monosccarides Through Their Activated Stannylene Acetal Intermediates. Molecules 2005, 10, 772-782.

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