Abstract
Abstract The D-lyxo and D-ribo methyl-N-trifluoroacetyl-2,5,6-trideoxy-5-amino hexofuranosides (13) and (14) are accessible from carbohydrate-like acyclic C7 products 3 and 5, whereas the 3-C-methyl analog of 13 is prepared in similar way from 15. Azide treatment of the toluensul-phonate ester at position 4 of methyl-2,6-dideoxy-3-C-methyl-L-ribo hexopyranoside (21), using hexamethylphosphoric acid triamide as cosolvent, gives rise to a mixture of azido derivatives in which prevails the arabino material (24), formed from 21 via inversion of configuration at positions 4 and 5.Product 24 gives rise to the 5-amino sugar derivative 28. The enantiomers of 13 and 14 are accessible from D-allo threonine and L-threonine, respectively.
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