Skip to main content
. Author manuscript; available in PMC: 2013 May 2.
Published in final edited form as: J Am Chem Soc. 2012 Apr 18;134(17):7545–7552. doi: 10.1021/ja3018187

Table 1.

Stereoselective glycosylations between donor 17 and various acceptorsgraphic file with name nihms-371173-t0001.jpg

Entry ROH Product Yield[b] α:p[c]
1 graphic file with name nihms-371173-t0002.jpg 29 91% >15:1
24
2 graphic file with name nihms-371173-t0003.jpg 30 62% >25:1
25
3 graphic file with name nihms-371173-t0004.jpg 31 89% α only
26
4 graphic file with name nihms-371173-t0005.jpg 32 67% >15:1
27
5 graphic file with name nihms-371173-t0006.jpg 33 72% α only
28
a

1,3,5-Trimethoxybenzene, Tf2O, DTBMP, molecular sieves 4 Å, −10 °C, 30 min, then add acceptor, −40 °C to room temperature, 16 h.

b

Isolated yields of the α/β mixture of disaccharide products.

c

The α/β ratios were determined by the integration of key signals in the 1H NMR spectra of the disaccharide products after purification by LH-20 size exclusion chromatography.