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. Author manuscript; available in PMC: 2014 Sep 15.
Published in final edited form as: Nat Chem. 2013 Sep 8;5(10):886–893. doi: 10.1038/nchem.1746

Figure 6. Rationalizations of the stereochemical outcome of glycosylation reactions with trioxacarcinose A and B donors.

Figure 6

Axial addition to the stereoelectronically favored half-chair 36 is relatively less impeded by steric interactions than addition to the alternative conformer 37, offering one rationalization for the high α-selectivities observed in glycosylation reactions of trioxacarcinose B donor 5 (see text for another). Similar considerations apply to explain the highly α-selective couplings of trioxacarcinose A donors 3 and 23.