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2005
Carbohydrates
U 0500
Synthesis of 1,6-Anhydro-2,3,4-trideoxy-2,3-epimino- and 1,6-Anhydro-2,3,4-triand Their NMR and Infrared Spectra. —
12- 209 deoxy-3,4-epimino-β-D-hexopyranoses
The synthesis of aziridine derivatives of carbohydrate, cf. epimines (VI) and (XII), can
be characterized as the transformation of an oxirane derivative into the aziridine derivative through the change of configuration on both carbon atoms of the oxirane ring in
(II) and (VII), respectively. Dianhydride (II) reacts regioselectively with sodium azide
under diaxial splitting of the oxirane ring affording azide (III), whereas azidolysis of
(VII) also provides, in addition to diaxial splitting product (VIII), product (IX), formed
by "anomalous" diequatorial splitting of the oxirane ring. Reduction of the vicinal trans
azido tosylates (V), (X), and (XI) yields the stable epimine (VI), and the unstable epimine (XII), respectively. — (KARBAN*, J.; BUDESINSKY, M.; KROUTIL, J.;
Collect. Czech. Chem. Commun. 69 (2004) 10, 1939-1954; Inst. Chem. Process
Fundam., Acad. Sci. Czech Rep., CZ-165 02 Prague 6, Czech Republic; Eng.) —
H. Hoennerscheid
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