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Methyl-α‑d‑2-selenonyl Pent-2-enofuranoside: A Reactive Selenosugar for the Diversity Oriented Synthesis of Enantiomerically Pure Heterocycles, Carbocycles, and Isonucleosides

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NIAID Data Ecosystem2026-03-09 收录
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https://figshare.com/articles/dataset/Methyl_d_2_selenonyl_Pent_2_enofuranoside_A_Reactive_Selenosugar_for_the_Diversity_Oriented_Synthesis_of_Enantiomerically_Pure_Heterocycles_Carbocycles_and_Isonucleosides/2111659
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The construction of vinyl selenone on a furanoside led to a highly reactive synthetic intermediate methyl-α-d-2-selenonyl pent-2-enofuranoside composed of a masked aldehyde, an electron-deficient double bond along with an excellent leaving group. This new Michael acceptor on reactions with different nucleophiles afforded bicyclic azasugars, cyclopropanated carbohydrate, dihydrofuran- and dihydroisoxazole- substituted furanosides, and isonucleosides in moderate to good yields. Hydrolysis of the hemiacetal linkage of some of these modified carbohydrates afforded enantiopure aziridines, nitrocyclopropane, and dihydrofuran.
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2016-02-12
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