A highly diastereoselective synthesis of 4-octulose and 2-deoxy-4-octulose from a
-fructose derivative |
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Authors: | Isidoro Izquierdo María T Plaza Rafael Robles Concepcin Rodríguez |
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Institution: | Isidoro Izquierdo*, María T. Plaza, Rafael Robles,Concepción Rodríguez |
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Abstract: | Bishydroxylation of methyl 1 with osmium tetraoxide proceeded with extremed high diastereoselectivity to give only methyl 2. Configurations of the new stereogenic centers (C-2,3) in 2 were determined by degradation of the C-5,6,7,8 fragment to the well-known methyl 7. Transformation of 2 into the required 10, was achieved by a methodology that implied, protection to 8, reduction of the ester group in 8 to a hydroxymethyl group in 9, and finally deprotection to the free 10. On the other hand, epoxidation reaction on 11 afforded only the corresponding 2,3-anhydro derivative 12 with
configuration, as could be demonstrated by degradation to (S)-1,2,4-trimetoxybutane 16, which synthesis is reported herein. |
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