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• W1963839110 abstract "Kochetkov’s extensive investigations of glycosyl orthoester and their analogs as glycosyl donors revealed that the alkyl derivatives were plagued by competition between the departing alcohol and the incoming acceptor. n-Pentenyl orthoesters (NPOEs) obviate competition by sequestering the departing pentenyl alcohol as a 2-halomethyl tetrahydrofuran. Exquisitely regioselective glycosidations of diol acceptors can be carried out with NPOEs triggered specifically with Yb(OTf)3/NIS. However with Sc(OTf)3, double glycosidation is the major reaction. manno, gluco and galacto NPOEs have been investigated. The latter two, which require a different experimental procedure for the manno counterpart, also give an excellent regioselectivity with Yb(OTf)3, but the yields are much lower than with manno." @default.
• W1963839110 created "2016-06-24" @default.
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• W1963839110 date "2007-02-01" @default.
• W1963839110 modified "2023-10-12" @default.
• W1963839110 title "A study of n-pentenylorthoesters having manno, gluco and galacto configurations in regioselective glycosylations" @default.
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• W1963839110 doi "https://doi.org/10.1016/j.carres.2006.09.022" @default.
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