Unexpected role of O-2 "protecting" groups of glycosyl donors in mediating regioselective glycosidation |
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Authors: | Fraser-Reid Bert Lopez J Cristobal Radhakrishnan K V Mach Mateusz Schlueter Urs Gomez Ana M Uriel Clara |
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Institution: | Natural Products and Glycotechnology Research Institute Inc. (NPG), 4118 Swarthmore Road, Durham, NC 27706, USA. dglucose@aol.com |
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Abstract: | Glycosidation of several vicinal diols reveals that exquisite regioselectivity can be achieved by using 2-O-benzoyl n-pentenyl glycoside donors and/or their cyclic 1,2-ortho ester counterparts. The regioselective preferences for both are the same, although ratios and yields may differ. In stark contrast, glycosidation of the diols with the corresponding 2-O-benzylated donors gives poor, if any, regioselectivity. |
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