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New synthesis of 1,4-dideoxy-1,4-imino-d-galactitol from d-glucose propane-1,3-diyl dithioacetal

✍ Scribed by Duy-Phong Pham-Huu; Yonas Gizaw; James N BeMiller; Ladislav Petruš

Book ID
104232208
Publisher
Elsevier Science
Year
2002
Tongue
French
Weight
57 KB
Volume
43
Category
Article
ISSN
0040-4039

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✦ Synopsis

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-Dgalactose. 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.

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