Journal
TETRAHEDRON LETTERS
Volume 43, Issue 3, Pages 383-385Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0040-4039(01)02167-0
Keywords
dithioacetals; amino sugars; azasugars; pyrrolidines; Pd-catalyzed hydrogenations
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The treatment of 4-azido-4-deoxy-2,3:5,6-di-O-isopropylidene-D-galactose propane-1,3-diyl dithioacetal (derived from D-glucose) with mercuric chloride and mercuric oxide in aqueous acetone afforded 4-azido-4-deoxy-2,3:5,6-di-O-isopropylidene-D-galactose. Acid-catalyzed deprotection of the azido derivative, followed by catalytic hydrogenation and concomitant intramolecular reductive amination in the presence of 10% palladium on carbon, gave 1,4-dideoxy-1,4-imino-D-galactitol in good yield. (C) 2002 Published by Elsevier Science Ltd.
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