Abstract

Bicyclic diazasugar analogues of L-arabinose and D-ribose have been prepared and characterized by x-ray crystallography and NMR spectroscopy. The crystalline arabinose analogue is the β-anomer in the ring-flipped 1C 4 conformation ( 7), but in D 2O solution this is a minor component with the major being the α-anomer in the 4C 1 conformation ( 6). The crystalline ribose analogue is the β-anomer in the 4C 1 conformation ( 10) which is also the major component in D 2O solution and is accompanied by a minor form which is probably the α-anomer in the ring-flipped 1C 4 conformation ( 11).

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