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. Author manuscript; available in PMC: 2023 May 13.
Published in final edited form as: European J Org Chem. 2022 Apr 21;2022(18):e202200300. doi: 10.1002/ejoc.202200300

Table 1.

Optimization of glycosidations of SInMe donor 2 and SInAll donor 6 with 6-OH acceptor 13.

graphic file with name nihms-1846207-t0001.jpg
Entry Conditions [equiv.] Yield of 14
1 2, NIS (3.0), TfOH (0.8), rt, 19 h 60%
2 2 , NIS (4.0), TfOH (1.0), rt, 15 min 75%
3 2, NIS (4.5), TMSOTf (1.0), rt, 10 min 83%
4 2, Ag2CO3 (0.8), TMSOTf (4.0), rt, 3.5 h 70%
5 6, NIS (2.0), TMSOTf (0.2), rt,16 h 29%
6 6, NIS (3.0), TMSOTf (0.8), rt, 2 h 68%
7 6, NIS (3.0), TMSOTf (1.0), rt, 1 h 89%
8 6, NIS (3.0), TfOH (0.4), rt, 24 h 52%
9 6, NIS (3.0), TfOH (0.8), rt, 24 h 69%
10 6, NIS (3.0), TfOH (1.0), rt, 24 h 73%
11 6 , NIS (3.2), TfOH (1.0), rt, 1 h 94%
12 6, Ag2CO3 (1.0), TMSOTf (4.0), rt, 1 h 79%