Regioselective Synthesis of Vinylic Derivatives of Common Monosccarides Through Their Activated Stannylene Acetal Intermediates 英文参考文献.docVIP

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Regioselective Synthesis of Vinylic Derivatives of Common Monosccarides Through Their Activated Stannylene Acetal Intermediates 英文参考文献.doc

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Regioselective Synthesis of Vinylic Derivatives of Common Monosccarides Through Their Activated Stannylene Acetal Intermediates 英文参考文献

Molecules 2005, 10, 772–782 molecules ISSN 1420-3049 Regioselective Synthesis of Vinylic Derivatives of Common Monosccarides Through Their Activated Stannylene Acetal Intermediates H. Namazi, 1,2,* and R. Sharifzadeh 1 1 Lab of Dendrimers and Biopolymers, Faculty of Chemistry, University of Tabriz, Tabriz, P. O. Box: 51664, Iran 2 Research Institute for Fundamental Sciences, Tabriz, P. O. Box: 5154916371, Iran * Author to whom correspondence should be addressed; Tel: (+89) 411 3344273; Fax: (+89) 411 3344273; E-mail: namazi@tabrizu.ac.ir Received: 16 April 2004; in revised form: 4 November 2004 / Accepted: 6 November 2005 / Published: 31 August 2005 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. Keywords: Regioselectivity, monosaccharides, tin intermediates, acrylation and metacrylation. 773 Molecules 2005, 10 Introduction Carbohydrates are naturally occuring bioorganic compounds which are found in biological systems [1]. Carbohydrates are the most abundant cla