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. 2022 Jun 22;7(26):22938–22943. doi: 10.1021/acsomega.2c02955

Table 1. Reaction Condition Optimization of the Deacetylation of Compound 11a.

2.2.

entry reagents solvent T (°C) 12 (% yield)b (%) 12a (% yield)b (%)
1 K2CO3c MeOH/DCM r.t. to 40 °Cd 0 0
2 10% LiOH MeOH/DCM r.t. to 40 °Cd 30 25
3 10% NaOH MeOH/DCM r.t. to 40 °Cd 51 19
4 10% KOH MeOH/DCM r.t. to 40 °Cd 47 23
5 LiAlH4 THF 0 °C to r.t. 81 0
a

Reaction conditions: 11 (0.1 mmol), reagents (1.0 mmol, 10.0 equiv), solvent (3.0 mL, MeOH/DCM, v/v = 2:1), 16 h.

b

Isolate yield.

c

Saturated aqueous.

d

Stirred at room temperature for 10 h (no reaction), then rise to 40 °C and stirred for another 6 h.