A Convenient Route to Functionalized Branched-Chain Sugars Via a Tosyl-Epoxide Derivative |
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| Authors: | Thang Ton-That |
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| Institution: | Laboratoire de Chimie Bio-organique, URA 488 du CNRS , Université Montpellier II , Place E. Bataillon, 34095, Montpellier, France |
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| Abstract: | Abstract Starting from methyl 4,6-O-benzylidene-2-deoxy-α-D-ribo-hexopyranoside-3-ulose 1 and proceeding through its corresponding tosyl-epoxide derivative 2, various branched-chain sugars (3-8) were prepared by nucleophilic and reductive ring openings. The presence of the sulfonylated oxirane group was found to be compatible with chemical transformations of the benzylidene acetal group (9-11), allowing facile access to the 6-deoxyhexoses (12-13). |
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