Vol 10: Synthesis of new enantiopure polyhydroxyaminooxepanes as building blocks for multivalent carbohydrate mimetics.Report as inadecuate



 Vol 10: Synthesis of new enantiopure polyhydroxyaminooxepanes as building blocks for multivalent carbohydrate mimetics.


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This article is from Beilstein Journal of Organic Chemistry, volume 10.AbstractNew compounds with carbohydrate-similar structure carbohydrate mimetics are presented in this article. Starting from enantiopure nitrones and lithiated TMSE-allene we prepared three 1,2-oxazine derivatives which underwent a highly stereoselective Lewis acid-induced rearrangement to give bicyclic products in good yield. Subsequent reductive transformations delivered a library of new polyhydroxyaminooxepane derivatives. The crucial final palladium-catalyzed hydrogenolysis of the 1,2-oxazine moiety was optimized resulting in a reasonably efficient approach to a series of new seven-membered carbohydrate mimetics.



Author: Bouche, Lea; Kandziora, Maja; Reissig, Hans-Ulrich

Source: https://archive.org/







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