Journal
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
Volume 19, Issue 8, Pages 2195-2198Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmcl.2009.02.103
Keywords
alpha-Glucosidase inhibitor; Salacinol; De-O-sulfated salacinol; Thiosugar
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Funding
- MEXT (Ministry of Education, Culture, Sports. Science and Technology)
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Facile synthesis of de-O-sulfated salacinols (3) was developed by employing the coupling reaction of an epoxide, 1,2-anhydro-3,4-di-O-benzyl-D-erythritol (9) with 2,3,5-tri-O-benzyl-1,4-dideoxy-1,4-epithio-D-arabinitol (10) as the key reaction. The reported structure of a potent alpha-glucosidase inhibitor named neosalacinol (8), isolated recently from Ayurvedic medicine Salacia oblonga, was proved incorrect, and revised to be de-O-sulfated salacinol formate (3c) by comparison of the spectroscopic properties with those of the authentic specimen synthesized. Discrepancies and confusion in the literature concerning the NMR spectroscopic properties of salacinol (1) have also been clarified. (C) 2009 Elsevier Ltd. All rights reserved.
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