A formal total synthesis of deoxynojirimycin from D-glucitol

This report deals with the formal synthesis of deoxynojirimycin using D-glucitol as an inexpensive starting material. Through a sequence of several selective protection/deprotection and nucleophilic substitution reactions, many isopropylidene derivatives were obtained. Formation of an epoxide interm...

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Bibliographic Details
Published in:Journal of the Brazilian Chemical Society 2003-10, Vol.14 (5), p.822-827
Main Authors: Braga, Raquel M., Kato, Lucilia
Format: Article
Language:English
Subjects:
CHEMISTRY, MULTIDISCIPLINARY
D-glucitol
deoxynojirimycin
glycosidase inhibitors
isopropylidene derivatives
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Summary:This report deals with the formal synthesis of deoxynojirimycin using D-glucitol as an inexpensive starting material. Through a sequence of several selective protection/deprotection and nucleophilic substitution reactions, many isopropylidene derivatives were obtained. Formation of an epoxide intermediate and its subsequent ring opening, via intramolecular nucleophilic substitution, leads to the synthesis of heterocyclic 1,5-dideoxy-1,5-diamine-2,3-O-isopropylidene-6-silyl-D-glucitol, which is a precursor of deoxynojirimycin (DNJ).
ISSN:0103-5053
1678-4790
DOI:10.1590/S0103-50532003000500019