E-resources
Peer reviewed
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Kilonda, Amuri; Compernolle, Frans; Peeters, Koen; Joly, Gert J; Toppet, Suzanne; Hoornaert, Georges J
Tetrahedron, 02/2000, Volume: 56, Issue: 7Journal Article
1-Amino-1-deoxy- d-glucitol ( 14) was converted to the N-Boc-2,3;5,6-di- O-isopropylidene derivative 16 which was transformed further into the selectively protected 2,3- O-isopropylidene 6-azido piperidine 3. The synthesis proceeded via a double inversion at C-5 involving internal attack of 4-OH to form the 4,5-epoxide 28, and ring opening of this epoxide by 1-NH 2 to generate the piperidine 3. This served as a valuable precursor of various target compounds, i.e. 6-azido- and 6-amino-1,6-dideoxynojirimycin 4 and 5, and the mono- and bicyclic derivatives 6– 12.
