Die kristall- und molekülstrukturen von drei thermodynamisch benachteiligten 2,6-anhydronitroalditolen (“Glycopyranosylnitromethanen”)

4,8-Anhydro-1,2,3,5-tetradeoxy-D-allo-non-1-enitol

“…However, in the overwhelming majority of these, the ring is in the chair conformation that places the hydroxymethyl group equatorially, which is also the usual case for O-glycosides. The only examples of C-glycosides with the inverted-chair conformation are the glycosyl amides, (IV) and (V) (Sundaralingam et al, 1982), and the glycosyl nitromethane derivative, (VI) (Kopf et al, 1990). Also of note is that glycosylamide (VII) adopts a skew-boat conformation in the crystalline state (Watson et al, 1993).…”