Influence of O6 in mannosylations using benzylidene protected donors: stereoelectronic or conformational effects?
TG Frihed, MTC Walvoort, JDC Codee… - The Journal of …, 2013 - ACS Publications
The stereoselective synthesis of β-mannosides and the underlying reaction mechanism
have been thoroughly studied, and especially the benzylidene-protected mannosides have
gained a lot of attention since the corresponding mannosyl triflates often give excellent
selectivity. The hypothesis for the enhanced stereoselectivity has been that the benzylidene
locks the molecule in a less reactive conformation with the O6 trans to the ring oxygen (O5),
which would stabilize the formed α-triflate and subsequent give β-selectivity. In this work, the …
have been thoroughly studied, and especially the benzylidene-protected mannosides have
gained a lot of attention since the corresponding mannosyl triflates often give excellent
selectivity. The hypothesis for the enhanced stereoselectivity has been that the benzylidene
locks the molecule in a less reactive conformation with the O6 trans to the ring oxygen (O5),
which would stabilize the formed α-triflate and subsequent give β-selectivity. In this work, the …
[引用][C] Influence of O6 in Mannosylations Using Benzylidene Protected Donors: Stereoelectronic or Conformational Effects?
FT Gylling, WM TC, CJ DC, A van der Marel Gijs… - 2013
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