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8
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33645918660
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note
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The strategy has been implemented in the synthesis of D-lividosamine (2-amino-2,3-dideoxy-D-glucose), a constituent of aminoglycosides lividomycin-A, lividomycin-B, etc. Diastereoselective equatorial addition of ammonia to 1α (Figure 1) followed by the desulfonylation of the product at the C-3 site produced a known intermediate for accessing D-lividosamine. Several partially and fully protected analogues of D-lividosamine could be synthesized using N-monoalkylated and N-dialkylated amines in a similar approach. See ref 2b.
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9
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0023698830
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10
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33645905818
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-
note
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All aminosugars 5a-c, 6a-c, and 7a-c described in Table 1 are single compounds. Structures of all compounds have been assigned on the basis of X-ray structural analysis and comparison of NMR data. These data will be reported elsewhere.
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11
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0033609760
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For a review on desulfonylation, see: Najera, C.; Yus, M. Tetrahedron 1999, 40, 10547.
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Najera, C.1
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26
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33645930121
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note
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One of the reviewers suggested that the drop in yield was possibly due to the amines irreversibly binding to the greater quantities of Ni(0) reagent present.
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