Syntheses of alpha- and beta-C-glucopyranosyl serines from a common intermediate |
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| Authors: | Nolen Ernest G Donahue Laurence A Greaves Rebecca Daly Trevor A Calabrese David R |
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| Institution: | Department of Chemistry, Colgate University, 13 Oak Drive, Hamilton, New York 13346, USA. enolen@colgate.edu |
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| Abstract: | A versatile synthesis leading to either C-linked alpha- or beta-glucopyranosyl serines is presented from a common, advanced synthetic intermediate. Cyclization of the penultimate carbinol onto the alkene and methanolysis of the lactone yields selectively the alpha-linkage. A transposition of these last steps leads to the beta-linked isomer selectively. |
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