ORGN 102 |
| Michael J. Panigot1, Angela R. Buckman1, Matt Whiteside1, and Jeremy Lamb2. (1) Department of Chemistry, Arkansas State University, PO Box 419, State University, AR 72467-0419, (2) Department of Chemistry and Physics, Arkansas State University, State University, AR 72467 |
| This project involves the preparation of thioglycoside containing dendrimers. These compounds may be useful in removing heavy metals found in the environment, such as lead based paint, and those found in tobacco. The sulfur atom of the thioglycoside should provide better metal coordination than oxygen based on HSAB theory. The carbohydrate provides water solubility and possibly molecular recognition. The synthetic objective is the first generation dendrimer. It can be prepared by reaction of 1,3,5-tristhiomethylbenzene with a carbohydrate peracetate in the presence of a Lewis acid such as BF3 etherate. Carbohydrates that will be investigated include glucose pentaacetate and galactose pentaacetate. 1,3,5-Tristhiomethylbenzene can be prepared from commercially available triesters by reduction to the triol using LiAlH4, conversion to the tribromide using either PBr3, and reaction of the tribromide with thiourea followed by base hydrolysis. After formation of the thioglycoside, hydrolysis of the acetate groups will provide the desired product. |
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New Reactions and Methodology, Metal-Mediated Reactions, Heterocycles and Aromatics
8:00 PM-10:00 PM, Sunday, March 28, 2004 Anaheim Convention Center -- Hall A, Poster
Division of Organic Chemistry |