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Synthesis of 2-azido-6-amino and 2-fluoro-6-amino analogs of 1-deoxynojirimycin

โœ Scribed by Kilonda, Amuri; Compernolle, Frans; Hoornaert, Georges J.

Book ID
127156549
Publisher
American Chemical Society
Year
1995
Tongue
English
Weight
651 KB
Volume
60
Category
Article
ISSN
0022-3263

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The Synthesis of 6-Azido and 6-Amino Ana
The Synthesis of 6-Azido and 6-Amino Analogues of 1-Deoxynojirimycin and their Conversion to Bicyclic Derivatives
โœ Amuri Kilonda; Frans Compernolle; Koen Peeters; Gert J Joly; Suzanne Toppet; Geo ๐Ÿ“‚ Article ๐Ÿ“… 2000 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 214 KB

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