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  • Title: Synthesis and conformational studies on methyl 4-O-acetyl-3-azido-2,3,6-trideoxy-hex-5-enopyranosides of the L series.
    Author: Liberek B.
    Journal: Carbohydr Res; 2005 Sep 05; 340(12):2039-47. PubMed ID: 16005860.
    Abstract:
    Methyl 3-azido-2,3-dideoxy-alpha-D-xylo-, -alpha-D-lyxo-, and -beta-D-xylo-hexopyranosides were converted into 4-O-acetyl-3-azido-6-iodo-2,3,6-trideoxy analogues via 6-O-p-tolylsulfonyl compounds. The elimination of hydrogen iodide from 6-iodo glycosides yielded methyl 4-O-acetyl-3-azido-2,3,6-trideoxy-beta-L-erythro-, -alpha-L-threo-, and -beta-L-threo-hex-5-enopyranosides. The configuration and conformation of all products are evaluated in depth on the basis of (1)H and (13)C NMR data. Factors determining conformational energy in 4-O-protected-3-azido-2,3,6,-trideoxy-hex-5-enopyranosides are discussed.
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