Carbohydrate mimic of 2-deoxystreptamine for the preparation of conformationally constrained aminoglycosides |
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Authors: | Guuske F Busscher |
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Institution: | Institute for Molecules and Materials, Organic Chemistry, Radboud University Nijmegen, Toernooiveld 1, 6525 ED Nijmegen, The Netherlands |
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Abstract: | The synthesis of a carbohydrate mimic of 2-deoxystreptamine (2-DOS) is described starting from d-ribose. Crucial steps of the synthesis involve a stereoselective nitroaldol condensation and deoxygenation via elimination-in situ reduction. Moreover, glycosylation of the carbohydrate 2-DOS derivative with a phenyl thioglycoside donor in the presence of TTBP and AgOTf followed by ring-closing metathesis yielded a conformationally restricted aminoglycoside analogue. |
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