Abstract
(Chemical Equation Presented) Several new stereoisomers of 3,4,6-trihydroxyazepanes and 7-hydroxymethyl-3,4,5-trihydroxyazepanes as well as known 3,4,5-trihydroxyazepanes were synthesized as potent glycosidase inhibitors from D-(-)-quinic acid in an efficient manner. The key step employs dihydroxylation of protected chiral 1,4,5-cyclohex-2-enetriols under RuCl3/NaIO4/phosphate buffer (pH 7) condition, followed by reductive amino cyclization. We found the choice of an appropriate protecting group to Cl-OH of chiral 1,4,5-cyclohex-2-enetriols would increase the yields of cyclization. The preliminary biological data indicate some of these azepanes possess potent inhibition against α-mannosidase and α-fucosidase.
Original language | English |
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Pages (from-to) | 4258-4261 |
Number of pages | 4 |
Journal | Journal of Organic Chemistry |
Volume | 72 |
Issue number | 11 |
DOIs | |
State | Published - 25 05 2007 |
Externally published | Yes |