Skip to main content
. Author manuscript; available in PMC: 2011 Sep 23.
Published in final edited form as: Carbohydr Res. 2010 Jul 21;345(14):2074–2078. doi: 10.1016/j.carres.2010.07.030

Table 3.

Comparisons of α selectivities for various donor-acceptor pairs

Entry Donor Acceptor Product Conditions Yield[a] Ratio[b] (α/β)
1 2 graphic file with name nihms224302t1.jpg
9
graphic file with name nihms224302t2.jpg
1031
TMSOTf rt 79% 8.2
2 2 9 10 HClO4-SiO2 rt 81% 19
3 2 graphic file with name nihms224302t3.jpg
11
graphic file with name nihms224302t4.jpg
1232
TMSOTf 0°C 96% 6.1
4 2 11 12 HClO4-SiO2 0°C 94% 8.1
5 2 graphic file with name nihms224302t5.jpg
13
graphic file with name nihms224302t6.jpg
14
TMSOTf 0°C 84% 13
6 2 13 14 HClO4-SiO2 0°C 86% 32
7 graphic file with name nihms224302t7.jpg
15
11 graphic file with name nihms224302t8.jpg
1633
TMSOTf 0°C 93% 3.0
8 15 11 16 HClO4-SiO2 0°C 90% 3.0
9 15 11 16 HClO4-SiO2 rt 85% 4.0
10 15 13 graphic file with name nihms224302t9.jpg
1734
TMSOTf 0°C 84% 4.0
11 15 13 17 HClO4-SiO2 0°C 88% 9.3
12 graphic file with name nihms224302t10.jpg
18
11 graphic file with name nihms224302t11.jpg
1935
TMSOTf 0°C 85% 3.0
13 18 11 19 HClO4-SiO2 0°C 88% 10
[a]

Combined yield of both anomers after purification

[b]

Determined by 1H NMR spectroscopy