TABLE 3.
Effect of acyl donor structure on the acylation of polydatin catalyzed by Fe3O4-PDA-TLL.
| Entry | Acyl donor | Acyl group | V0 (mM/h) | Time (h) | C (%) | OH a -regioselectivity (%) |
|---|---|---|---|---|---|---|
| 1 | Vinyl butyrate |
|
9.8 ± 0.4 | 14.0 | 98.1 ± 0.1 | 100 |
| 2 | Vinyl crotonate |
|
4.7 ± 0.1 | 18.0 | 90.1 ± 0.2 | 100 |
| 3 | Vinyl pivalate |
|
n.d | 6.0 | ― | ― |
| 4 | Vinyl hexanoate |
|
12.3 ± 0.4 | 14.0 | 98.1 ± 0.4 | 100 |
| 5 | Vinyl sorbate |
|
6.3 ± 0.2 | 18.0 | 91.3 ± 0.3 | 100 |
| 6 | Vinyl benzoate |
|
n.d | 6.0 | ― | ― |
| 7 | Vinyl octanoate |
|
12.4 ± 0.3 | 14.0 | 98.4 ± 0.2 | 100 |
| 8 | Vinyl 2-ethylhexanoate |
|
n.d | 6.0 | ― | ― |
| 9 | Vinyl decanoate |
|
12.6 ± 0.4 | 14.0 | 98.7 ± 0.5 | 100 |
| 10 | Vinyl undecenoate |
|
13.9 ± 0.5 | 14.0 | 98.8 ± 0.6 | 100 |
| 11 | Vinyl laurate |
|
13.7 ± 0.6 | 14.0 | 99.1 ± 0.5 | 100 |
| 12 | Vinyl myristate |
|
12.8 ± 0.3 | 14.0 | 97.5 ± 0.3 | 100 |
| 13 | Vinyl palmitate |
|
12.6 ± 0.2 | 14.0 | 97.5 ± 0.4 | 100 |
| 14 | Vinyl stearate |
|
11.2 ± 0.3 | 14.0 | 96.0 ± 0.5 | 100 |
The reactions were carried out at 55°C and 200 rpm by adding 0.03 mmol polydatin, 0.33 mmol vinyl donor, 180 mg Fe3O4-PDA-TLL, into 3.0 ml anhydrous MeTHF.
Primary hydroxyl.