Table 1. Glycosylation reactions with isothiocyanate 2[a][b].
Entry | Acceptor | Product, Yield, selectivity |
---|---|---|
1 |
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2 |
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3 |
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4[c] |
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5 |
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Bn = benzyl, Bz = benzoyl, isothiocyanyl sialyl = [methyl (4,7,8,9-tetra-O-acetyl-3-deoxy-5-isothiocyanyl d-glycero-d-galacto-α,β-nonulopyranosid)onate].
unless otherwise stated all reactions were conducted at -78 °C with 1.2 equiv of acceptor in 2:1 dichloromethane:acetonitrile.
After glycosylation the crude reaction mixture was acetylated to facilitate purification.