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. 2017 Apr 12;82(9):4793–4811. doi: 10.1021/acs.joc.7b00470

Table 2. Competitive Donor Activations.

graphic file with name jo-2017-00470e_0006.jpg

entry donor I donor II productsa yieldb (%)
1 1 2 1C/2C, 14:1 65
2 1 3 1C/3C, 1:0 80
3 2 3 2C/3C, 6:1 37
4 3 4 3C/4C, 1.6:1 39
5c 4 5 4C/5C, 1:0 64
a

Determined by 1H NMR spectroscopy of the isolated disaccharide.

b

The disaccharide fraction was quantified after isolation by size-exclusion chromatography and related to the limiting amount of NIS (see Experimental Section).

c

The combined donor concentration was 0.1 M, triflic acid was added at −20 °C, the reaction mixture was heated to +15 °C overnight, and then the reaction was quenched (Et3N).