Table 1. DAF Yields from Gal-dA According to Various Alkyl Alcoholsa.
yield
(%) |
||||
---|---|---|---|---|
entry | R | 2,5-DAFb | 2,3-DAFb | total |
1 | CH3(CH2)3– | 63 | 30 | 93 |
2 | CH3(CH2)4– | 62 | 23 | 85 |
3 | CH3(CH2)5– | 54 | 21 | 75 |
4 | CH3(CH2)6– | 40 | 21 | 61 |
5 | CH3(CH2)7– | 35 | 17 | 52 |
6 | (CH3)2CH(CH2)2– | 62 | 32 | 94 |
7 | CH3(CH2)3CH(C2H5)CH2– | 35 | 11 | 46 |
Reaction conditions: Gal-dA (3.0 g, 14 mmol), alcohol (324 mmol), H2SO4 (40 wt %), PX (3.5 g, 33 mmol), 160 °C (reflux), 10 h.
Isolation yield.