Journal
CARBOHYDRATE RESEARCH
Volume 342, Issue 3-4, Pages 490-498Publisher
ELSEVIER SCI LTD
DOI: 10.1016/j.carres.2006.09.022
Keywords
n-pentenylorthoesters; regioselective glycosidation; lanthanide triflates
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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. (c) 2006 Elsevier Ltd. All rights reserved.
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