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Paper | Regular issue | Vol 71, No. 8, 2007, pp.1787-1800
Published online, 25th May, 2007
DOI: 10.3987/COM-07-11066
Stereoselective Synthesis of D-1-Deoxynojirimycin and Its Stereoisomers

In Su Kim, Ho Young Lee, and Young Hoon Jung*

*College of Pharmacy, Sung Kyun Kwan University, 300 Jangangu, Chonchondong, Suwon 440-746, Korea


A stereoselective synthesis of D-1-deoxynojirimycin (1), D-1-deoxymannojirimycin (2), and D-1-deoxyallonojirimycin (3) was achieved via the regioselective and diastereoselective amination of anti-1,2-dibenzyl ether using chlorosulfonyl isocyanate (CSI), ring-closing metathesis, diastereoselective dihydroxylation, and the regioselective stereochemical inversion of the resulting diol.