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. Author manuscript; available in PMC: 2018 May 27.
Published in final edited form as: J Org Chem. 2017 Dec 22;83(1):374–381. doi: 10.1021/acs.joc.7b02768

Table 3.

Glycosidation of Donors 14 and 16 with Different Acceptors in the Presence of TMSOTfa

graphic file with name nihms967691u4.jpg
Entry Donor Acceptor (R”) HOFox (equiv.) Time Product Yield (α/β ratio)
1 graphic file with name nihms967691t15.jpg graphic file with name nihms967691t16.jpg 0
0.25
1 h
1 h
graphic file with name nihms967691t17.jpg 93% (α-only)
99% (α-only)
2 14 graphic file with name nihms967691t18.jpg 0
0,25
3 h
3 h
graphic file with name nihms967691t19.jpg 27% (α-only)
85% (α-only)
3 14 graphic file with name nihms967691t20.jpg 0
0,25
6 h
2 h
graphic file with name nihms967691t21.jpg 13% (α-only)
98% (α-only)
4 14 graphic file with name nihms967691t22.jpg 0
0.25
3 h
3 h
graphic file with name nihms967691t23.jpg 14% (α-only)
86% (α-only)
5 14 graphic file with name nihms967691t24.jpg 0
025
3 h
3 h
graphic file with name nihms967691t25.jpg 25% (α-only)
92% (α-only)
6a 14 graphic file with name nihms967691t26.jpg 0
0.25
6 h
2 h
graphic file with name nihms967691t27.jpg 20% (α-only)
68% (α-only)
7 graphic file with name nihms967691t28.jpg 18 0
025
0.5 h
0.5 h
graphic file with name nihms967691t29.jpg 61% (10/1)
90% (10/1)
8 16 20 0
0.25
0.75 h
0.75 h
graphic file with name nihms967691t30.jpg 26% (α-only)
92% (α-only)
9 16 22 0
0.25
0.75 h
0.75 h
graphic file with name nihms967691t31.jpg 27% (36/1)
91% (20/1)
10 16 24 0
0.25
0.75 h
0.75 h
graphic file with name nihms967691t32.jpg 14% (12/1)
85% (12/1)
a

TMSOTf (0.15 equiv).