Journal
TETRAHEDRON LETTERS
Volume 52, Issue 29, Pages 3802-3804Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2011.05.063
Keywords
DNJ; Miglustat; Miglitol; Mitsunobu reaction; Double inversion strategy
Categories
Funding
- National Basic Research Program of China (973 Program) [2007CB914403]
- Natural Science Foundation of China [20802037]
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A novel and facile synthesis of a series of the biologically significant iminosugar derivatives including 2-deoxynojirimycin, Miglustat and Miglitol is reported. The synthesis features a strategic double inversion mechanism for securing the desired stereochemistry at C5 position of such glucose-type carbohydrate mimetics, representing a practical and remarkable improvement on the previously reported method that suffers from the loss of the stereo-control during the reaction process. Crown Copyright (C) 2011 Published by Elsevier Ltd. All rights reserved.
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