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. Author manuscript; available in PMC: 2011 Feb 19.
Published in final edited form as: J Org Chem. 2010 Feb 19;75(4):1095–1100. doi: 10.1021/jo9021474

Table 3.

Competitive activations of S-ethyl glycosyl donors: 1c (armed) vs. 2c (superarmed)

graphic file with name nihms174299u4.jpg
Entry Temp. Time Ratio 4:5 a Yield 4 b (α:β) Yield 5 b (α:β)b
1 rt 1 h 1:0.8 53% (1:1.7) 45% (β only)
2 −10 °C 1 h 1:2.4 22% (1:4) 51% (β only)
3 −25 °C 3 h 1:4 14% (1:4) 62% (β only)
4 −35 °C 24 h 1:1.5 11% (1:5) 26% (β only)
a

– determined by comparing integral intensities of the corresponding signals in the NMR spectra recorded for the crude reaction mixtures;

b

– isolated yields