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Synthesis of l - altro -1-Deoxynojirimycin, d - allo- 1-Deoxynojirimycin, and d - galacto- 1-Deoxynojirimycin from a Single Chiral Cyanohydrin

✍ Scribed by van den Nieuwendijk, Adrianus M. C. H.; Ruben, Mark; Engelsma, Sander E.; Risseeuw, Martijn D. P.; van den Berg, Richard J. B. H. N.; Boot, Rolf G.; Aerts, Johannes M.; Brussee, Johannes; van der Marel, Gijs A.; Overkleeft, Herman S.


Book ID
126219163
Publisher
American Chemical Society
Year
2010
Tongue
English
Weight
230 KB
Volume
12
Category
Article
ISSN
1523-7060

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Synthesis of 1,5-dideoxy-1,5-imino-d-ara
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The title, 1,5-dideoxy-l,5-imino-D-arabinitol (2), was synthesized in seven steps from Darabinose with 5-azido-5-deoxy-o-arabinofuranose as key intermediate and 40% overall yield. An affinity procedure employing the N-carboxypentyl derivative of 2 linked to aminohexyl agarose permitted the isolation