Sialic acid-containing glycoconjugates are natural products with a wide variety of biological functions and therefore very important synthetic targets. Sialylation reactions to form sialic acid glycosidic bonds are still challenging. The study of O-protecting groups in the mainstream of carbohydrate chemistry occupies a very important niche and represents the major venue to control reactivity and stereocontrol of glycosyl donors. However, O-substitution of sialic acids, beyond traditional acetates, and the effect that O-substituents may have on the outcome of sialylation remains practically unknown. Recently, we showed that introduction of TBDMS and benzoyl substituents at O-4 produces very interesting and rather unpredictable sialyl donor properties. As part of a broader research project on the effect of O-protecting groups in sialic acid chemistry, herein we present the synthesis of novel sialyl donors bearing at C-4 monochloroacetyl group and testing them for the synthesis of sialic acid containing glycoconjugates. We also report the development of a methodology to selectively introduce substituents at C-7.
|Advisor:||De Meo, Cristina|
|Commitee:||Dixon, Robert, Lu, Yun, Shabestary, Nahid|
|School:||Southern Illinois University at Edwardsville|
|School Location:||United States -- Illinois|
|Source:||MAI 56/03M(E), Masters Abstracts International|
|Subjects:||Chemistry, Organic chemistry|
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