Реакция #6520

Уравнение реакции

17

(2R,5S)-1-[2-(Butyldiphenylsiloxymethyl)-1,3-oxathiolan-5-yl]cytosine

tetrabutylammonium fluoride

→

3

Выход 75.0%

(2R,5S)-1-[2-(Hydroxymethyl)-1,3-oxathiolan-5-yl]cytosine

Выход 75.0%

Растворители

THF

THF

Условия реакции

Обработка

1. 1
   Другоеthe disappearance of starting material (30 min)
2. 2
   КонцентрированиеThe reaction mixture was concentrated under reduced pressure
3. 3
   Другоеthe residue purified by preparative TLC

Методика

To a solution of the β anomer 17 (0.15 g, 0.32 mmol) in THF (25 mL) was added tetrabutylammonium fluoride 1M in THF (0.35 mL, 0.35 mmol, 1.1 eq) and the reaction was allowed to stir at room temperature until TLC indicated the disappearance of starting material (30 min). The reaction mixture was concentrated under reduced pressure and the residue purified by preparative TLC using 12% MeOH/CHCl3 as development solvent to give 0.055 g (75%) of 3 from ethyl ether/MeOH (trace) as a white crystalline solid. [α]23D =-121.6 (c 1.1, MeOH) (for the S,R isomer 2 [α]23D =120.96 (c 1.06, MeOH)); 1H NMR: ((CD3)2SO) δ 3.03 (dd, J5,4a =4.4 Hz, J4a,4b =11.86 Hz, 1 H, 4a-H), 3.43 (dd, J5,4b =5.3 Hz, J4a,4b =11.86 Hz, 1 H, 4b-H), 3.80 (app t on D2O exchange goes to d, J2,2-CH2-OR =4.17 Hz, 2 H, 2-CH2 -OH), 5.27 (t, J2-CH2,OH =4.6 Hz, 1 H, 2-CH2OH), 5.22 (t, J2,2-CH2-OH =4.17 Hz, 1 H, 2-H), 5.88 (d, J5,6 =7.47 Hz, 1 H, H-5), 6.21 (app t, J=5.05 and 4.84 Hz, 1 H, 5-H), 7.19 (bs, 2 H, NH2), 7.89 (d, J5,6 =7.47 Hz, 1 H, H-6).

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