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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
 

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On the Influence of the C2-O2 and C3-O3 Bonds in 4,6-O-Benzylidene-Directed beta-Mannopyranosylation and alpha-Glucopyranosylation.

The synthesis of 4,6-O-benzylidene-protected 2-deoxyarabino-, 3-deoxyarabino-, and 3-deoxyribothioglycosides is described and their glycosylation reactions, with activation by either 1-benzenesulfinyl piperidine/trifluoromethansulfonic anhydride or diphenyl sulfoxide/trifluoromethanesulfonic anhydride, studied. In contrast to the corresponding 4,6-O-benzylidene-protected glucosyl and mannosyl donors, which are alpha- and beta-selective, respectively, poor diastereoselectivity is observed in all cases. The reasons for this poor selectivity are discussed in terms of the interaction between the C2-O2 and C3-O3 bonds in the glucosyl and mannosyl donors and of the influence of this interaction on the ease of formation of the intermediate glycosyl oxacarbenium ions.[1]

References

  1. On the Influence of the C2-O2 and C3-O3 Bonds in 4,6-O-Benzylidene-Directed beta-Mannopyranosylation and alpha-Glucopyranosylation. Crich, D., Vinogradova, O. J. Org. Chem. (2006) [Pubmed]
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