Table 1.
Glycosylation using glycosyl donors with various ester-protecting groups at C2
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Acceptors | |
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1a P=Ac X= O-trichloroacetimidateb | 84% (α:β 1:1) | NA |
1b P=Bz X= O-trichloroacetimidateb | NA | 86% (α only) |
1c P = ClCH2CO X = O-trichloroacetimidateb | NA | 85% (α only) |
1d P=CH3OCO X = O-trichloroacetimidateb | 85% (α:β 1:1) | 83% (α only) |
1e P = (CH3)3CCO X = O-trichloroacetimidateb | 80% (α only) | 81% (α:β 2:3) |
1f P = (CH3)3CCO X = SPhc | NA | 82% (α:β 1:3) |
Compound 1a–e, R1 = Ac, R2 = Ac; compound 1f, R1:R2 = CHPh.
Activation with TMSOTf.
Activation with NIS/AgOTf.