Skip to main content
. 2019 Jan 3;84(3):1218–1227. doi: 10.1021/acs.joc.8b02536

Table 1. Results of the Substitution Reaction of TES-d with the 4-Oxo- and 4-Thiofuranosides.

graphic file with name jo-2018-025365_0005.jpg

  X = O X = S
  α/β ratio (exp)ab α/β ratio (comp) α/β ratio (exp)cb
riboside >98:2 94:6 91:9
arabinoside <2:98 2:98 8:92
xyloside 85:15 68:32 69:31
lyxoside <2:98 0:100 3:97
a

Reagents and conditions: 2 equiv of TES-d, 1.3 equiv of TMSOTf, −78 °C, 7 days.

b

The α/β ratio was established by NMR spectroscopy.

c

Reagents and conditions: 2 equiv of TES-d, 1.3 equiv of TMSOTf, −30 °C, 10 days.