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  • Title: Unexpected role of O-2 "protecting" groups of glycosyl donors in mediating regioselective glycosidation.
    Author: Fraser-Reid B, Lopez JC, Radhakrishnan KV, Mach M, Schlueter U, Gomez AM, Uriel C.
    Journal: J Am Chem Soc; 2002 Apr 03; 124(13):3198-9. PubMed ID: 11916390.
    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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