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A new class of glycosidase inhibitor: synthesis of salacinol and its stereoisomers



A new class of glycosidase inhibitor: synthesis of salacinol and its stereoisomers



Journal of Organic Chemistry 66(7): 2312-2317



Salacinol (4) is one of the active principles in the aqueous extracts of Salacia reticulata that are traditionally used in Sri Lanka and India for the treatment of diabetes. The syntheses of salacinol (4), the enantiomer of salacinol (5), and a diastereomer (7) are described. The synthetic strategy relies on the selective nucleophilic attack of 2,3,5-tri-O-benzyl-1,4-anhydro-4-thio-D- or L-arabinitol at C-1 of 2,4-O-benzylidene D- or L-erythritol-1,3-cyclic sulfate. The work serves to resolve the ambiguity about the exact structure of salacinol and establishes conclusively the structure of the natural product.

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Accession: 045079417

Download citation: RISBibTeXText

PMID: 11281771

DOI: 10.1021/jo001444g


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