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Journal article

Total Asymmetric Syntheses of D-Lividosamine and 2-Acetamido-2,3-Dideoxy-D-Arabino-Hexose Derivatives

The "naked sugar" (+)-(1R,4R)-7-oxabicyclo[2.2.1]hept-5-en-one ((+)-2) has been converted to D-lividosamine ((+)-i: 3-deoxy-D-glucosamine) and derivatives via (+)-2-chloro-2,3-dideoxy-5,6-O-iso-propylidene-D-arabino-hexono-1,4-lact one ((+)-33) and (4)-2-azido-2,3-dideoxy-5,6-O-isopropylidene-D-ribo-hexono-1,4-lactone ((+)-34) in a highly stereoselective fashion. Similarly, 2-acetamido-2,3-dideoxy-D-arabino-hexose and derivatives were derived from the "naked sugar" (-)-(1S,4S)-7-oxabicyclo[2.2.1]-hept-5-en-2-one ((-)-2) via the double hydroxylation of the C-C double bond in (-)-N-benzyl-N-[(1R,2S,4S)-6-bromo-7-oxabicyclo[2.2.1]hept-5-en-2-endo-y l]amine ((-)-40).

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