Synthesis of 3,5-O-Benzylidene-2-deoxy-L-riboaldose from 5,5-Dihydroxy-2-phenyl-1,3-dioxane |
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| Authors: | Trond Ulven Per H. J. Carlsen |
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| Affiliation: | Department of Organic Chemistry , Norwegian University of Science and Technology , N-7034, Trondheim, Norway |
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| Abstract: | The asymmetric alkylation of 2-phenyl-1,3-dioxan-5-one was achieved via the RAMP-hydrazone. Regeneration of the ketone followed by setreoselective reduction and ozonolysis, gave the protected 2-deoxy-L-ribose, 3,5-O-benzyldiene-2-deoxy-L-erythro-pentoaldose with 98% e.e. Removal of the benzylidene yielded the unnatural 2-deoxy-L-ribose. |
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| Keywords: | antibacterial drug Cefdinir impurities synthesis |
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