Bicyclic diazasugars 2. Synthesis and structures of L-arabinose and D-ribose analogues

• Published in: Tetrahedron Vol. 54; no. 20; pp. 5097 - 5104
• Main Authors: Berges, David A., Hong, Liwu, Dalley, N.Kent
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 14.05.1998; Elsevier
• Subjects: Aminals; Carbohydrate mimetics; Chemistry; Chemistry, Organic; Diaza compounds; Enzyme inhibitors; Physical Sciences; Science & Technology; X-Ray crystal structures; X-Ray crystal structures; Enzyme inhibitors; Diaza compounds; Carbohydrate mimetics; Aminals; aminals; carbohydrate mimetics; X-ray crystal structures; diaza compounds; INHIBITORS; enzyme inhibitors; CASTANOSPERMINE
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/S0040-4020(98)00249-X

Bicyclic diazasugar analogues were prepared in two steps from the respective sugars and characterized by x-ray crystallography and in D 2O solution by NMR spectroscopy. 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).