Synthesis of 3,5-O-Benzylidene-2-deoxy-L-riboaldose from 5,5-Dihydroxy-2-phenyl-1,3-dioxane

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 y...

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Published in:Synthetic communications 2000-07, Vol.30 (13), p.2275-2280
Main Authors: Ulven, Trond, Carlsen, Per H. J.
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Language:English
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description 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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title Synthesis of 3,5-O-Benzylidene-2-deoxy-L-riboaldose from 5,5-Dihydroxy-2-phenyl-1,3-dioxane
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