Darstellung neuartiger Carbosilan- und Polyether-Glycodendrimere

Boysen, Mike M. K.

In the course of this thesis, novel carbosilane and polyether glycodendrimers were prepared. These structures are potential inhibitors of mannose binding lectins of E. coli. Further, the access to these glycodendrimers was evaluated in view of synthetic chemistry. A tetravalent carbosiloxane glycodendrimer was prepared via alcoholysis of a chlorosilane with a hydroxyethyl glycoside, the corresponding tetravalent carbosilane derivative was synthesised via hydrosilylation of an allyl glycoside with a hydrosilane. Polyether glycodendrimers with a glycerol scaffold were prepared via a reaction sequence containing Williamson etherification with 3-chloro-2-chloro-methyl-1-propene followed by trans-formation of the double bond at the focal point of the molecule via a ozonolysis-reduction protocol to a secondary alcohol. By introduction of glycol ether spacers between glycerol units more spacious glycerol glycol ethers could be obtained. For both types tetravalent glycodendrimers could be prepared in good yields and syntheses were carried out on a multigramm scale, while the octavalent compounds were obtained only in low yields.



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Boysen, Mike: Darstellung neuartiger Carbosilan- und Polyether-Glycodendrimere. 2003.


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