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  • Title: Addition of amines and carbon nucleophiles to vinyl sulfone-modified 6-deoxy-hex-3-enopyranoside: a case of nucleophile dependent diastereoselectivity.
    Author: Bhattacharya R, Pathak T.
    Journal: Carbohydr Res; 2009 Nov 23; 344(17):2336-41. PubMed ID: 19815185.
    Abstract:
    Reactions of amines and carbon nucleophiles with 4-sulfonyl-hex-3-enopyranoside generate a range of C-3 amino- and C-3 branched-chain sugars, which are analogues of 3-amino-3,6-dideoxy sugars and 3-C-branched-chain-3,6-dideoxy sugars. The diastereoselectivity of addition reaction is nucleophile dependent; while both nitrogen and carbon nucleophiles added in cis-fashion, amines generated C3-C4 trans-diaxial products (gulo-derivatives), and carbon nucleophiles afforded C3-C4 trans-diequatorial products (gluco-analogues).
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