. Author manuscript; available in PMC: 2021 Aug 12.

Published in final edited form as: Chem Rev. 2020 Jul 5;120(15):7104–7151. doi: 10.1021/acs.chemrev.0c00243

Table 15.

The O3→O2 Migration in Protected Acyl Galactopyranosides and the O2→O3 Migration in Protected Acyl Glucopyranosides.^a

Method^a	Temp. (°C)	Time (h)	Yield (%)
A	75	7	80
B	75	8	83
A	40	10	77
B	40	12	79
A	60	7	76
B	50	12	76
A	r.t.	48	68
B	45	24	71
A	75	7	74
B	50	17	78
A	r.t.	48	60
B	r.t.	24	67
A	r.t.	48	70
A	50	24	71
B	50	12	72

Method A: Ag₂O, TBAI, DMF; Method B: CsO₂CCF₃, TBAI, DMF.