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. Author manuscript; available in PMC: 2009 Feb 25.
Published in final edited form as: Tetrahedron Lett. 2008 Feb 25;49(9):1542–1545. doi: 10.1016/j.tetlet.2007.12.105

Table 1.

AgBF4 promoted glycosylations of glycosyl acceptors 12–15.

graphic file with name nihms40112t1.jpg
entry D A time product yield, % α/β ratio
1 1 13 24 h 17a -a -
2b 1 13 16 h 17a 91 1.4/1
3c 1 13 5 h 17a 95 2.0/1
4 2a 13 5 min 17a 92 2.4/1
5 2b 13 5 min 17b 96 β only
6 2b 14 24 h 18b 82 β only
7 3a 13 10 min 17a 89 1.2/1
8 3b 13 10 min 17b 91 β only
9 3b 14 15 min 18b 84 β only
10 3c 13 15 min 17c 91 1.6/1
11 4a 15 5 min 19a 87 7.4/1
12 4b 13 20 min 17b 90 β only
13 5a 13 5 min 17a 95 1.3/1
14 5a 14 5 min 18a 92 1.4/1
15 5b 13 10 min 17b 90 β only
16 5c 13 20 min 17c 75 1.2/1
17 6 13 24 h 17a -a -
18d 6 13 24 h 17a 91 1.2/1
19e 6 13 10 min 17a 92 1.2/1
20 7 13 24 h 17a -a -
21d 7 13 24 h 17a 89 1.0/1
22e 7 13 20 min 17a 76 1.2/1
23 8 13 5 min 17a 97 1.6/1
24 8 12 10 min 16a 91 1/3.4
25 9 13 20 h 17a 81 2.0/1
26 9 15 1.5 h 19a 81 2.3/1
27 10 13 24 h 17a -a -
28 11 13 5 min 17a 80 1/1.5
29 11 12 2 days 16a 65 1/5.4
a

no product formation was detected; all glycosylations were promoted with AgBF4 except the following:

b

3.0 equiv. of BF3-Et2O was used

c

3.0 equiv. of BF3-Et2O and 0.5 equiv. of AgBF4 was used

d

2.0 equiv. of NIS was used

e

2.0 equiv. of NIS and 0.5 equiv. of AgBF4 was used.