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. Author manuscript; available in PMC: 2016 Jan 19.
Published in final edited form as: Angew Chem Int Ed Engl. 2014 Nov 28;54(4):1275–1278. doi: 10.1002/anie.201409797

Table 1. Glycosylation reactions with isothiocyanate 2[a][b].

Entry Acceptor Product, Yield, selectivity
1 graphic file with name nihms647077t1.jpg
2 graphic file with name nihms647077t2.jpg
3 graphic file with name nihms647077t3.jpg
4[c] graphic file with name nihms647077t4.jpg
5 graphic file with name nihms647077t5.jpg
[a]

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].

[b]

unless otherwise stated all reactions were conducted at -78 °C with 1.2 equiv of acceptor in 2:1 dichloromethane:acetonitrile.

[c]

After glycosylation the crude reaction mixture was acetylated to facilitate purification.